


Becoming the Penguin

by BlessedMasochist, ReginaCordum13



Category: Gotham (TV)
Genre: Dysphoria, M/M, Trans Male Character, Trans Oswald Cobblepot, Transphobia, dead naming
Language: English
Status: In-Progress
Published: 2019-03-10
Updated: 2019-07-30
Packaged: 2019-11-15 01:12:27
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 25,655
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18063734
Author URL: https://archiveofourown.org/users/BlessedMasochist/pseuds/BlessedMasochist, https://archiveofourown.org/users/ReginaCordum13/pseuds/ReginaCordum13
Summary: This fic will be a re-telling, of sorts, of the story of Oswald Cobblepot from before the pilot in season 1. How he came to be in Fish Mooney's employ, his developing relationship with Fish and Butch, and the fallout. The desired image of a respectable, powerful man is an ambition that might lead him to ruin, or it could help to transform him more than he ever thought possible.





	1. Chapter 1

The trendy, elusive nightclub was everything it had been rumoured to be; a throbbing baseline churned from oversized speakers as florescent blue lights glowed overhead, making the almost empty club seem like a dream. Beneath their ghostly light, girls took their turns dancing for one of the most powerful mobsters in Gotham, bodies ethereal and lovely as they turned and swayed. The red damask wallpaper lining the room gave the impression of wealth and refinement, belying the seedy Gotham underbelly, the back-alley dealings done with a sinful smile— guileful and cold— that the underboss was known for. Creeping in slowly from the back, a small, weaselly individual found themselves standing before the club’s owner: Fish Mooney. Their knees trembled beneath the loose fabric of stolen slacks two sizes too big; blue eyes wide with intimidation.

Fish looked at the young freckled creature before her. She was unimpressed with the interruption to rehearsals to say the least. Dark hair obscuring a pale, shy face, frame too small to be of much use, clearly frightened of their own shadow, still it showed quite a lot of mettle to seek an audience this way. “What is your name, my sweet?” she asked in a kind, crooning voice. Her long, painted nails tapped a high powdered cheekbone, as she sat back in her chair with ease. Someone from the bar handed her a drink without a word spoken, or request from her dark lips.

“Os-O-Oliva, ma’am,” came the reply, regret visibly punctuated with a wince.

Fish Mooney rose from her seat, approaching with a slowly raised brow. She looked over the person who stood before her in a visibly cheap suit. The tie was poorly done up around their neck, knot crooked and loose; her gaze steadily rose, dissecting every pucker of fabric and loose thread until at last she looked deep into their eyes, light blue and very afraid, but with a spark of determination that would not easily be extinguished. This person intrigued Fish Mooney much more than the scantily clad dancers behind them. “What is your real name, sugar?”

It was incredibly difficult to keep his chin up under her intense gaze, knowing her sharp eye had picked him apart; the awkward, squared swell of his chest, the soft round of his cheeks, the curve of his hip despite the jacket obscuring his frame. “Oswald, I-I would prefer Oswald,” he, definitely he then, gulped, exhaling softly in relief. “Oswald Cobblepot.”

“Then Oswald you shall be,” she replied concisely with a wave of her hand, turning away from him to resume her seat.

She was beautiful, the epitome of power and refinement, and more beautiful still, in his mind, as she granted him this identity without fuss. With a quiet, utterly grateful whisper of thanks, he moved to kneel by her side, not wishing to obstruct her view of the stage as they spoke.

His immediate reverence delighted her, and she reached out to stroke the soft line of his cheek with a curious gentleness. “Why did you come to my humble club, Oswald?” she asked with a tender grin.

“My friend, an old co-worker… he told me if I had the right skill, I might be able to find work that paid well here. I won’t lie to you and pretend that I have a vast repertoire, but I am a very skilled pianist,” he answered, voice unnaturally gruff.

It had been ages since the club had auditioned a pianist— her grin widened. “Play something for me then, sugar.” She sat back, arms crossed over her chest expectantly. She clapped her hands, the dancers immediately stopping their movements to vacate the stage en masse.

A large man stood behind Fish, raising a brow at the young man as he scampered up onto the stage, gait awkward and twitchy as he moved to stand before the shiny black piano. “We auditionin' more entertainment today, Boss?”

“We are now, Butch. This is Oswald. I'm quite taken with him~”

Oswald's eyes widened in fear and amazement as he surveyed the impossibly huge man that hulked behind Fish from his vantage on the dimly lit stage, feeling incredibly foolish in comparison. Nervously, he tugged on his tie, tightening it as he turned slowly back to sit at the piano, fingers poised carefully before beginning their dance across the smooth keys. A delightfully jazzy tune sprung forth, one that Oswald had practiced countless times before; in his mind’s eye he sat dressed in a tailcoat with shiny shoes and a cane leaned against a baby grand. He would smile confidently as he entertained his guests, mouth twisting around a glimmering cigarette holder clamped between his teeth. They would all adore and respect him. The lively jive melded seamlessly into a rainy-day tune, then finished with a more classical number; all-in-all it was a well-rounded audition.

Fish smirked, watching Oswald through lidded eyes. When he was through with his little performance, she and Butch clapped. “Well, Oswald I believe congratulations are in order~ How would you like to play tomorrow night?”

“I would be delighted, Miss Mooney,” he replied, beaming from ear to ear as he bent at the waist in a small bow; his cheeks were rosy, stomach filled to the brim with butterflies. “Thank you so very much for this opportunity, I won’t let you down.”

"Of course, we’ll have to clean you up. I cannot have you playing at my club looking like that."

His stomach sank. “Is...Is this not okay, Ms Mooney?” he asked softly, fiddling with the lining of his suit, voice betraying thinly layered disappointment. She had been so quick to agree upon his chosen name, was the suit really too much? Surely, she didn’t expect a dress!

Fish raised a perfectly manicured brow. “I expect all my employees to look their very best, Oswald. That suit will not do. Butch will take you to get a new one of higher quality, as well as a haircut, and any other accessories you may need.”

“T-thank you Miss Mooney...” he stammered, breathing a sigh of relief. His blue eyes were wide with hope and wonder at the goddess before him, imagining himself in a handsome pinstripe.

She grinned, and with a snap of her fingers Butch stepped forward to escort Oswald out.

He looked down at the young man critically, before looking ahead once more. “We'll take you to my tailor, Oswald. He'll take care of you.”

For the second time that day, Oswald found himself standing quite still as someone looked him over from head to toe, but with the confidence of victory he stood tall and proud as he followed after Butch. “I appreciate it, thank you, Butch. This was procured on... short notice. Can’t afford much on a delivery boy’s salary” he grimaced, tugging on the worn leather of his belt. The stolen suit was ill-fitting; the entire garment was two sizes too big, obscuring his frame almost entirely as it hung from his small frame.

“It's all right, Oswald. I didn't come from money either, I get it,” he replied easily with a shrug of his large shoulders.

They arrived at the tailor, a small little shop in the centre of the downtown Gotham area. When they entered Butch greeted the shop owner with a familiar smile and a handshake. “This is Oswald Cobblepot, Mr Fuji. He needs the works.”

Oswald's face split into a wide grin as he stuck out a small hand in greeting. “Please to meet you, sir.”

The short Japanese man merely nodded, and ushered Oswald out back through a sheer silk curtain, away from Butch without a word. Only once inside the fitting room did the elderly man speak. His voice a soft rasp, “Undress to your underwear, boy. I need to take measurements.”

Oswald balked at the instruction, frozen before the three-fold mirror as he made dreaded eye contact with his reflection. “Couldn’t you just measure over?” he asked nervously, unbuttoning the large suit jacket slowly, with the thud of his heartbeat deafening in his red ears. He removed it and held it awkwardly in his hands for a moment before depositing it on the floor.

“No. It will affect my measurements” the tailor replied stoutly, motioning for Oswald to continue as he unrolled a thin plastic tape measure and pulled a small notepad from his apron.

Swallowing, he opened the front of the shirt. Beneath it lay a dirty, off white tank, atop which an entire roll of cloth bandages had been hastily wrapped, partially obscuring an unnatural swelling of the fullest part of his chest. His eyes held fast to the floor as the wrinkled button up joined the jacket on the floor.

His veins felt like ice, embarrassment enveloping him with an unforgiving chill. As his fingers moved to undo his belt, he exhaled softly in defeat, brow furrowing as he stood before the mirror in a dingy pair of gym shorts. He chewed his lower lip, feeling quite ugly.

As the clothing slid off the slim shoulders Daisuke was able to fully understand the boy. He was not a boy at all and yet he was not the first of his kind that he had ever served, and not the first in Gotham to need a nice suit. He did not necessarily approve of such a lifestyle, but business was business, and the boy seemed to work for Carmine Falcone. Had his protection through Fish, at least, and Daisuke certainly did not wish to lose his life over semantics.

“Have you ever been measured before Oswald?”

“No sir...” The boy shook his head, still pointedly avoiding the mirror as he fidgeted with his hands. Subconsciously, he held his arms out stiffly to obscure his front side. He wished he could block out the reflected shape of his frame in his peripheral vision. His hair hung in long, blunt chunks— clearly the product of a hasty decision.

The tailor nodded and set to work. “This will be a bit of a problem,” he murmured, gesturing to his chest. “It'll mess with the measurements.”

Oswald was far inside his head, staring blankly at the tailor for a moment. “Do you... do you need me to take it off?” he asked quietly, sounding miserable, but polite.

“Yes, it's wrapped unevenly.” Such bindings would make an accurate cut difficult, as the depth of the bind seemed to vary in spots and would most likely be different day-to-day.

The boy winced, brows pushing together in a deep furrow as his fingertips moved over the first thin metal clasp that held the bandages taut. He caught his own eyes in the mirror, heart sinking into his knees as the clips were removed and the tight wrapping slowly unwound.

He wanted the suit.

The relief that accompanied such freedom was usually pleasant in a way, but as the weight of his chest shifted downward Oswald felt nothing but embarrassment— the hanging deposits of fat were prominent beneath his thin white undershirt with nothing to keep them hidden.

Daisuke said nothing as the bandages were removed. He wrapped the tape around the high part of chest, where the breastbone met the sternum. He tsked, shifting to his knee as he wrapped his tape around his slim frame; he looked at the bruising around his ribs. “Do you always bind in such a poor manner?”

Oswald's skin crawled as the tape crossed over his chest and then down under his breast, jaw unconsciously tightening.

“Poor?” he replied softly, voice a timid squeak, “I don’t know any way of doing it differently...” It felt strange to discuss so casually, Oswald thought absently, staring into the floorboards.

“I can make you a suit that would hide some of your less-desirable features if that is something you want?”

“Y-yes please, thank you,” he replied quickly, feeling as though he had been exposed far too many times for one day. There were many things he found undesirable about himself, and he doubted that a suit could hide them all.

Daisuke did the rest of the measurements expeditiously, and then left Oswald to get dressed. He told Butch the suits would be ready within the week and that his normal fee would be billed to the club.

The moment he was alone Oswald scrambled for his trousers, yanking them on quickly and threading the old leather belt around his hips before bending down to retrieve the long, crumpled pile of cloth bandage. His pink lower lip stuck between his teeth as he stood before the mirror, carefully winding it back around his chest. With each pass he pulled it taut, holding his breath to keep it tighter still before fastening the end; the pressure around his ribcage was uncomfortable, but ignored.

Soon he emerged, happy to be dressed but feeling entirely silly dressed in the poorly fit suit, unable to keep from comparing himself to the well-dressed men displayed in photographs around the waiting area.

“Thank you, sir,” he mustered, hands deep in the pockets of his coat.

Butch clapped him on the shoulder and escorted him out. “Next is your hair, Oswald.”

“My hair?”

Yes, he supposed that could use a bit of help. Frustrated with his appearance and the constant tangle of his long, disagreeable locks, the small man had cut most of it off in a fit of upset; the angle of the scissors was prominent in the choppy, uneven clumps that had been cut.

Butch simply nodded and took him to a small corner parlour where he greeted everyone by name. “Hey Jimmy, I want you to give Oswald here the number 6, okay? Looks like someone took a lawnmower to the poor kid’s head. Fix him up.”

“Sure thing, Butch. Sit in the third chair, kid. I'll be right with you~” A burly man with a shaved head smiled and gestured to the chair.

Chuckling softly at Butch's joke, he sank into the chair, faced with his reflection once more. How he detested the round shape his face took on— even his cheekbones seemed round! If he stuck out his chin a bit it resembled a jawline but as always, it faded when he relaxed. The boy huffed, feeling miserable with himself once more, sitting up straight as he watched the patrons of the small shop through their reflections in the mirror. Oswald looked over the barber for a moment as he moved through the shop, in awe of his size and physique. Gotham certainly grew its men large, he thought 'Some of them anyway...'

Butch took a seat, legs spread in a relaxed position as he picked up a newspaper. Soon the barber came over and began to make idle chatter. “Jeeze kid, someone did a number on your head. Did you piss off your last barber?”

“Uhm, fell asleep at the wrong party,” he lied with a convincing smile, willing his voice as deeply as it would go.

The barber nodded with a laugh. “I think we've all done that a time or two~! We'll fix you right up, son.”

“I would appreciate that very much, my mother’s been nagging me about it,” Oswald replied, feeling an odd twist of excitement and nervousness; he kept his gaze low, hoping that when he looked again, he would find himself transformed somehow, as though a haircut alone would make all the difference.

Jimmy turned him around away from the mirror and began working. The buzz of a razor drowned out whatever inane drabble the barber was spewing and twenty minutes later he turned Oswald around to face the mirror. The sides of his hair were shaved only serving to highlight how round his jaw truly was. “There you go, pretty boy.”

Oswald's leapt into his throat and then plummeted into his stomach. “Thank you...” he murmured, managing to keep a pleasant expression, though his mind was screaming.

'I look like a lesbian in drag!'

It was horrid, his hopes dashed by the caricature before him; being called pretty was the final blow, and he stood suddenly. “Butch, I apologize, I realize I haven't phoned my mother, she'll be worried...”

Butch's expression shifted from bemused to utterly unimpressed. “Fish is gonna expect you back at the club, Oswald...”

“Yes, of course,” he nodded, smile pained, “I just need a few moments to check in with her, perhaps I stop home for lunch and return?” Oswald suggested, desperate for a moment alone.

He sighed softly, disappointed in the young man.

“O-Or I could go back with you,” he stated slowly, voice wavering dangerously as his throat grew tight. He could feel his mind starting to race, a familiar blankness beginning to envelop his brain.

“Good choice,” he replied, grabbing him by the shoulder and escorting him from the parlour with a wave to Jimmy. “What the fuck was that, kid?” he asked once they were outside. “We give you a bunch of shit and you try to leave? Ms Mooney won't like to hear about that.”

Butch's grip made him gasp, wincing as he was forced outside.

“I'm so-sorry...” he hiccupped, blue-green eyes welling with tears. “I-I just need a minute alone, pl-please...” It was horrifying, finding himself entirely out of control. Blackness tinted the edge of his vision, slowly surrounding him, encroaching on his peace of mind. It was too much, the hair, Fuji’s cold hands touching his torso, Butch’s unimpressed expression looking down at him. He wanted to leave, why wouldn’t he let him leave! “I was going to come back, I promise!” His voice climbed high as he began to cry, chest aching sharply with each sobbing breath.

Butch pushed him into an alley out of sight, sneering in disgust. “Kid, kid, calm down, Jesus.”

Trembling, Oswald pressed back flat against the brick wall, looking absolutely frightened as he wiped at his reddened cheeks. “I'm sorry...”

Butch pressed a hand against the kid’s chest in an attempt to calm him down, then froze and snatched it back. “What the f-” His eyes widened.

“Don't touch me!” He hissed, fear turning to a defensive anger. He tried to push Butch away, small frame trembling against the wall as Butch held him against it.

Butch looked down at Oswald’s red, tear-streaked face, large hand pressed against his chest. Something wasn’t adding up about him. Who cries over a new suit and a haircut?

“Sorry, kid...” He mumbled. “Just calm down, all right? I ain't trying to hurt you. Why are you crying anyway?”

“I don't like the haircut, it makes my face look horrid,” he admitted bitterly, wiping at an errant tear with a quick, furious swipe.

“Really, Oswald?” he asked with a raised eyebrow, looking at the smooth curve of his jaw and cheek, the slope of his neck, and his small dainty hands as they grasped the short dark strands. He sighed, coming to understand why the kid was so upset. “It looks a lot better than whatever happened to your head before.”

“I know it does, I just-” he cut himself off with a heavy sigh, “I guess I was hoping it would... help”.

He sighed clapping him on the shoulder. “It's a haircut, kid, not a miracle. Come back to Fish, she can help you.”

He nodded mutely, breath finally evening out. “Sorry for my... outburst,” he murmured hoarsely.

He shrugged and turned, not wishing to discuss the scene the boy had just made. He was confident now Oswald would follow him back to Fish without a fuss. They walked for a little while in silence before arriving back at the club. Fish was at the back table with three well-dressed men, in deep negotiation. Butch went to her side immediately, leaning to whisper in her ear. She grinned and looked up at Oswald. “Gentleman, excuse me a moment.” She stood and approached her new pianist. “Oswald~”

Oswald admired their attire wistfully, managing a faint smile when Fish stood before him “Hello, Miss Mooney— thank you again for your generosity,” he said, still feeling inwardly uncomfortable.

She grinned with a soft tilt of her cheek. “Nothing in life is free, child. Go play us something~ Something soft and lilting.”

“Absolutely,” Oswald replied, as he knew this was the reply she expected to receive. Holding his head high, he stepped up onto the raised stage and seated himself at the piano.

With a steadying breath, he filled the room with a quiet, almost mournful tune, burying his thoughts deep within the melody, eyes falling half shut as his fingers moved over the keys.

She returned to the table and smiled at the men, falling back into the steep negotiations. “Where were we?”

“We are not giving up the warehouse by the docks, Mooney, and Falcone is crazy to think Don Maroni would just roll over.”

She sat back, leg crossed at the knee, elbow up on the top of booth. “Gentlemen, we don't expect Maroni to roll over, we will still allow him to run his clubs near the docks in exchange for the warehouse,” she smirked softly with a gesture of her hand.

“Allow!?”

She held up a hand, silencing them with ease. “It's simple, the warehouse, or the clubs. Don Falcone will expect your Don's answer by tomorrow.” She dismissed them with a wave of her hand, Butch rising to make certain they followed her unspoken command.

Slowly, he was drawn from his tumultuous thought, ears prickling as the intense conversation carried.

The melody changed, shifting to something bolder, more victorious.

Fish stood and went to the bar ordering two drinks. She then approached the stage and handed Oswald a drink. “Come down here a moment, son.”

He took the glass with a small smile, sliding off the end of the stage with a soft grunt, managing to keep from sloshing. “Yes ma'am?”

She sat on the edge of the stage, legs crossed at the knee. “I have a few questions for you.”

He stood before her once again, clutching the glass tightly in one hand. “Yes?” he replied, eyebrows raised.

“How far is it you wish to go with this?” She gestured to his form.

“Until... Until I can look in the mirror and be happy with what I see, proud even,” he answered after a lengthy pause.

She nodded in understanding. “You know I see a lot of myself in you; there's a drive, ambition. I want to help you, Oswald.”

“...Really?”

Oswald could scarcely believe that a stranger would want to help with something so deeply personal. He trembled before her, this goddess who whispered her blessing over him.

She smiled and ran her fingers through his new hair. “I want you to return here tomorrow by four. We have a lot of work to do~”

“Yes ma'am,” he replied, eyes fluttering shut for a moment as her manicured nails scraped at his scalp. He looked up at Fish one last time, light blue eyes taking in the face of the woman who had been so impossibly kind to him. With a soft goodbye, he turned and left, promising to be back at the designated time next day.

Butch came up beside her, watching as Oswald left. “Kid seems quite taken with you, boss.”

“All the better, loyalty is such a difficult trait to come by in Gotham, Butch. I am fortunate that my staff love me.” She turned, placing a gentle hand on his cheek.

“Yes, Fish,” he murmured with a soft smile, dark eyes warmly meeting hers.

Oswald returned home, breathing in the warm, delicious scent of dinner as he slipped inside, locking the door behind him. “There is my handsome Oswald!”

His mother emerged from the narrow kitchen, gasping in delight as she spotted his hair, promptly running her fingers over the short sides. “Oh, my little cobble pot, you look so nice... I am glad you have your hair fixed, it looks much better like this.”

His heart swelled with joy as his dear mother showered him with affection. It had come as a pleasant surprise that Gertrud was completely accepting of his desire to be himself. She had held him close as he cried, brushing the messy clumps of hair from his shoulders after he attacked his long hair with scissors and broke the bathroom mirror. She had always wanted a son to care for her in her old age and was delighted to know that she would forever remain the most beautiful woman in their home; she was his entire world and he loved her with all his heart.

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	2. Chapter 2

**Summary for the Chapter:**

> Oswald learns that Fish's love isn't free.

The next evening, Oswald returned to the nightclub as promised, dressed in khaki slacks and a pilled sweater vest. Underneath, he wore the rumpled button up from the previous night, white fingers pulling at the bottom of the garment tremulously. Fish looked at him raised brow, breathing a heavy sigh through her mouth. Blinking twice she stood from the table with an air of incredulity, arms crossed over his chest. “No, absolutely not, Oswald.”

“Pardon?” he asked, eyes owlishly wide.

“Stephano, Butch,” she called, ignoring the young man for the moment. Oswald simply gaped at her, wondering if the gangster had changed her mind about helping him on a whim simply by looking at him. The two appeared from the back of the bar, hands folded respectfully in front of them. “Take Oswald and find better clothes. I need him to look presentable for Carmine tonight!”

Carmine.

He had picked up on that name the previous night: a powerful man.

Her men simply nodded, escorting Oswald to the back rooms from a connecting hallway under the stage. There was a small lounge, with two large armoires, one filled with suits, too large to fit poor Oswald’s small frame. The other was a small stockade of weapons, large munition guns, back up magazines, and more bullets than one could count.

“This way, Oswald, I think Jimmy might have somethin’ for ye.” Oswald was quickly moved away from the small green room, and through to another back room. It was cramped and smelled of garlic and brussels sprouts. A smaller, spindly man looked up from the gun he was polishing. “What?”

“Fish wants him in better clothes, you got any?”

“In the back,” he answered with a sneer, dark glassy eyes following Oswald as they led him towards a hanging set of clothes.

Butch looked at Oswald and pressed the clothes into his hands, “Bathroom’s that way, kid,” he murmured, pointing to the next door on their left.

Relieved, Oswald went to change in private. He returned after some time in a pair of freshly pressed black slacks and a deep purple button up that fit much better than the second-hand one he was wearing previously. A pair of shiny black shoes finished the look. It was nothing like the pressed suits the others were wearing, nor the fitted uniforms of Miss Mooney’s other employees, but the cut of the trousers, and the forgiving lines of the shirt made Oswald feel a little more at home in his skin. Though he wished he could have done something about the smell.

“Miss Mooney, we're back!” he called, feeling rather confident in the new, stylish outfit.

“Good boy!” she beamed, touching his cheek with a gentle palm. “Get up on that stage, son, and play me something smooth and light~”

“Yes Miss Mooney~” he smiled, climbing up the stairs with renewed self-assurance. A beautiful melody unfolding from his fingertips at her request.

After fifteen minutes an older gentleman, surrounded by men in dark suits, entered the club.

“Carmine~” Fish purred, gliding over to kiss each cheek.

“Fish, the club is looking well.” He spoke with an air of one who knew the sort of power he wielded. He was a man used to getting what he wanted when he wanted it. He was a dangerous man, highly intelligent and aloof.

“Business is good, yes~”

“Good to hear.” He surveyed the club, a critical eye looking everything over. There was a young man at the piano whom he had never seen before, curious blue eyes watching him and Fish. “Who is the new kid?” he asked, gesturing up to the stage.

“That is my new boy Oswald. He's a beautiful joy on the piano.”

Oswald gaged the crowd, ears straining to listen over the steady sound of his music. He wanted to know more about Carmine. The man was all at once everything he wanted to be, and an impossible image to obtain. How could one command such a presence? Even Fish seemed in awe of him.

Carmine nodded with a soft smile. “You always did have good taste. Let us sit.”

They sat by the stage and began to discuss business. Carmine telling Fish about Don Maroni's plans of refusal, gently rebuking her for overplaying her hand.

“It's all a part of the plan, Carmine. By the end of the week I'll have their clubs and the warehouse.”

He raised a brow. “I shall be very disappointed if your plan does not work, Fish.”

Oswald continued to play, catching bits of their discussion during the ebb of the melody.

“I understand, sir,” she murmured, finishing her drink.

They sat in silence for a song or two. Carmine stood after another drink, and bidding Fish goodnight with a kiss to the crown of her head, said his goodbyes, “Be safe, Fish. Goodnight.” He turned back with a soft smile in her direction. “You've finally found a good pianist.”

Oswald was delighted, smirking to himself from his seat at the piano, fingers playing across the ivories impishly before finally coming to rest.

Once Don Falcon was gone Fish crooked two fingers in Oswald’s direction, wanting him beside her. He hopped down quickly, at her side in an instant. “How was I, Miss Mooney?” he asked, vying for her approval.

“Wonderful, sweet boy, Carmine was very impressed~”

He beamed, a gentle flush gracing his sweat-glistened cheeks. “I am so happy to hear that.”

“What do you think of Carmine Falcone, Oswald~?”

“I can tell he is a very powerful man, just by the way he moves. Everything he does is deliberate and confident...”

“Just the sort of man you'd like to be someday, right, Oswald?” she asked with a smile and a knowing look.

“Oh yes,” he replied emphatically. He could only dream of being so powerful. Don Falcone had Gotham at his fingertips, with all the influence and money he could ever want- people respected him without question.

Her smile widened. “I need you to run an errand tomorrow.”

“Anything for you, ma'am,” Oswald smiled eagerly.

“I need you to go to the docks and pick up a package. You will go with Butch and make certain you two are not seen.”

“Is this to do with the deal with Maroni?” he asked slyly, revealing his skill for eavesdropping.

She raised a brow. “My, my, someone was listening to something he shouldn't have been~” she smirked. “Yes, it does, my sweet. It is a weapons shipment that dear Don Maroni very much needs.”

“I would be more than happy to assist you, Miss Mooney” he nodded, heart racing at the idea of participating in something so impressive.

“Good boy,” she breathed, petting his cheek. “You can be done for the night if you wish~ The dancers are beginning now.”

“May I buy you a drink, Miss Mooney?” he asked softly. Oswald did not have much money to spare, but he wished for any excuse to spend more time with the beautiful woman, to hear her low, sweet voice pamper his battered ego.

She grinned. “I would enjoy that, sweet boy.” She snapped her fingers and one was presented to her. “What would you like, Oswald?”

“Bourbon with blackberries and ginger ale?” he asked, heart fluttering.

She laughed, delighted. “What a charming order~” After a few moments one was brought to Oswald and handed to him.

“A friend recommended it to me, I'm simply addicted to the sweetness of the blackberries,” he explained with a soft laugh, burying his nose in the glass to take a hearty swig.

“I love a man who knows what he wants~” Fish replied. “I have a question for you.”

“Yes?” he invited with a small nod, taking a pre-emptive sip of his bubbling drink.

“Why did you come to my little club~?”

“A friend of mine told me that I could make good money here,” he said, tone implying that he knew all along that he would be participating in illegal activity.

She nodded with a smile. “I see. I want you to understand, Oswald that I can only be as good to you as you are to me. We're a family here.”

“Miss Mooney, I would do anything for you,” he breathed, blue-green eyes glowing in the lights from the stage as the women danced.

Her dark eyes glittered as she looked at the smitten young man before her. “You're a good boy, Oswald,” she breathed, stroking his hair.

He shivered slightly, leaning into the touch. It was so similar to the way his mother would coo at him and yet it felt electric, a familiar warmth blooming in the pit of his stomach. “I want to be, Miss Mooney.”

“Good, I expect absolute loyalty from my employees, Oswald.” She finished her drink and another one was presented to her. Her cheeks were becoming rosy now.

“You have accepted something that took me years to make peace with, even now I struggle and yet you smile at me and encourage me...” he tittered softly, taking a second drink from the bar staff. “You need not ask me for loyalty, you have it already.”

“Darling, here you can be anything you want to be. Gotham is a place of individuals, where the strongest survive. Never let anyone tell you who you are or what you can be.” She reached out, taking his hand.

He squeezed it, feeling quite confident as he pressed a gentle kiss to the smooth curve of the top of her hand.

She grinned, quite charmed. “You're quite the gentleman, Oswald~ I have another question for you, sweet boy.”

“Yes, Miss Mooney?”

“Do you like girls or boys?”

“Both... I think,” he answered honestly, tracing her knuckles with a rough thumb. “Though in the spirit of honesty I must admit I haven't had much experience with either...”

“I figured as much, but there's nothing wrong with that. You've the world at your fingertips, and a whole life ahead of you to enjoy.”

He nodded eagerly, drunk on bourbon and the confidence she had coaxed from within him. “You're right!”

She reached out and pet his hair, smiling at him, eyes warm and a but glassy from the drink. “You'll make a fine young man, Oswald. You best get home, you've a big day tomorrow~”

“Thank you for your time Miss Mooney...” he sighed happily, giving her a bow before slipping out the front door. He whistled, feeling giddy as he made his way back home.

Gertrud was already sleeping, and Oswald crept silently into his room, collapsing into bed with a satisfied groan, mind whirling. Just weeks before it had felt like his life was spiralling out of control, and suddenly he found himself so happy, and confident enough to flirt.

When Oswald arrived at the club the next day, Butch was waiting for him. Fish was nowhere in sight. “Ready Oswald? I’m driving.”

“Absolutely Mr Gilzean,” he replied, confidence from the previous night having carried over. He wore a black button up with a red tie, stretching his arms upward in an attempt to discourage the ache in his ribs.

He nodded, noting Oswald's pained expression. They got into an unmarked van, Oswald noting that this was not Butch’s normal vehicle. As they drove, they did not speak, a light jazz tune filled the silence between them as Oswald watched the city he loved through the window. The docks were on the border of city limits, industrial, grey, and bleak. When Butch parked, he looked at Oswald and removed his gun from its holster. “We go in, we take the goods, we leave. Got it? I'll do the lifting, you stand watch.”

“Yes sir,” he nodded, scanning the area immediately.

“Good kid.”

They left the vehicle, Oswald’s heart beating a mile a minute as they snuck around the back of the large shipping container. It looked old, and fully repurposed as a storage unit. Butch quickly broke the lock, as Oswald kept eyes on the surrounding area. Once inside he grabbed a small cache of papers, and a large box of weapons. “Let’s move,” he commanded quietly, pushing past Oswald to get back to the car.

Oswald opened the back, Butch pushing the box inside as if he were loading an ordinary carton of groceries, instead of hundreds of thousands of dollars in illegal firearms. As Butch was straightening up, a movement caught Oswald’s eye. He turned, and saw a flash of silver, knowing enough to push Butch to direct his attention to their attacker. His entire body froze for a moment.

“Kid, get down!” Butch cried, pushing Oswald into the van. He jumped in after him, Oswald scrambling on his knees to shut the doors as the gunfire continued.

“Shit, shit, shit,” Oswald breathed, chest tight as it fought against the constrictive bindings to take air. He didn’t have the reach he would if he had full range of motion in his ribs, and he struggled with the doors before they finally locked. Butch had already climbed into the front seat, the van lurching forward as they made their escape. Once free from danger, adrenaline still coursing through his veins, Oswald laughed, laying flat in the back of the van as he unconsciously rubbed at his sides. “Holy shit!” he grinned. Slowly, with a groan, he sat up, the bindings bunching uncomfortably around the bottom of this armpits. He made his way up front, coming to sit in the passenger’s seat, jaw tight.

If Butch noticed Oswald’s predicament he hadn’t said anything, which was a welcomed reprieve. “Not bad for a first run, kid.

“Thank you, Mr Gilzean,” he grinned. Oswald was thrilled with their victory, though he kept a close eye on their mirrors.

“Now we give the goods over to their destination, and report to Fish.”

They dropped the guns off at the back of an illegitimate laundromat, the owner of which was the man from Fish’s club, who stunk of garlic. He greeted them with a greasy smile and thanked them for the delivery, promising Fish the agreed upon double indemnity.

Oswald's heart had not quite settled down by the time they returned to the club, feeling invigorated by his first favour done for his new boss.

Butch whispered into Fish’s ear, presumably about the other thing he had surreptitiously taken from Maroni. He wondered idly if the guns had been the main target of their ‘mission’ or if whatever he had in his breast pocket was somehow the real prize.

Fish turned, sending Butch to the back rooms, and greeted Oswald with a smile and a kiss upon the mouth. “Oswald, my sweet boy, how was your errand?” she asked hand gentle upon his cheek

Oswald flushed deeply across the sharp angle of his freckled nose, eyes sparkling. “Very good, Miss Mooney. I kept careful watch for Mr Gilzean while he handled the pick-up and delivery,” he said promptly, careful to use innocuous terms as he nestled against her cool hand.

“Good boy, I knew I could count on you~”

The words rolled over him like rain from heaven, soothing the fires of contention in his head.

Good Boy

“Always Miss Mooney,” he beamed, happy to please her.

Fish grinned at him and then turned towards the bar. “Now, would you play me something triumphant, my little love~?”

Oswald nodded, flouncing to the piano all-too happily to play a lively march. A smile lingered on his lips as the music filled the room, feeling proud of himself.

Fish began to talk to Butch in low hushed tones, looking to Oswald with concern. Once the song ended she called him back to her side.

Oswald could not hear her but felt her eyes on him. When he had finished the piece, he slipped back down to stand before her with a small smile.

“Are you in pain, Oswald?” she asked softly, looking deep into his clear blue eyes.

“Pain?” he murmured, suddenly reminded of the dull ache in his chest. “It's nothing, Miss Mooney,” he insisted with a shallow exhale and an earnest smile. It was a pain that he had learned to slowly ignore, block it out just as he blocked out the layers of fat that lay below the bandages and the distinct inadequacy between his legs. It was surprising what one could disregard when they tried hard enough.

She raised a brow, noting the slight crease at the corners of his eyes, the tightening of his jaw and the way he held his shoulders, stiff and wide to distribute the weight that lied beneath the bandages. “Butch, take him to the clinic, I cannot have my star pianist in pain.”

“Clinic?” he asked, looking nervous. Despite his clear struggles with himself, Oswald had never attempted to receive any sort of help with his condition, out of stubbornness or fear was something he himself wasn’t certain of.

Butch nodded. “Come on, Oswald, I'll drive.”

Looking rather flighty, the small man followed after him, feeling quite nervous about the entire ordeal. It wasn’t as though he were ungrateful, in fact the opposite was true, but being open about his condition was something that made him feel incredibly vulnerable.

The ride to the clinic was as silent as the one to the docks, Oswald chewing his lower lip as he crossed his arms over his chest. Once they arrived Butch went in with him, giving them the Falcone credentials. They were admitted right away.

“What seems to be the trouble Mr...?”

“Cobblepot,” he provided stiffly, “Oswald Cobblepot.” Staring blankly at the doctor, Oswald struggled for a proper explanation for his 'trouble', ultimately opting for blunt truth, delivered between tightly grit teeth.

“I have breast and I would like to not have breasts.”

The doctor nodded and wrote a few things on the chart. “Have you ever been pregnant, and is there a possibility that you could be pregnant now?”

Flushing deeply, he shook his head firmly, rather mortified by the idea. In truth, Oswald had never participated in penetrative sex, feeling disconnected from his body in a way that made intimacy past kissing nearly impossible.

He nodded. “What is it you're using now, Mr Cobblepot?”

“Uhm... just a roll of bandages I nicked at the corner store,” he admitted, eyes trained on the faded tile flooring as he unconsciously inched back toward Butch.

“That is causing you some serious damage, Mr Cobblepot. I recommend a compression garment. We have a few that we can give you today. They're far better than the bandages you're using.”

“I would appreciate that, thank you,” Oswald replied, finally looking up. He managed a faint smile, though he still appeared uncomfortable with the situation.

Butch laid a gentle hand on his shoulder, large and warm through his thin shirt.

“Mr Gilzean would you give us the room?”

Oswald was stiff a moment but relaxed into the surprisingly comforting touch. “Thank you Butch,” he murmured softly “I'll be okay.” The last part was as much for himself as it was for Butch, feeling flighty at the thought of being left alone with the unfamiliar physician.

Butch merely nodded and left the room, closing the door on his way out.

“Now, Mr Cobblepot, please remove your top and the bandages.”

He knew it was coming, and did so quietly, fingers slowly undoing the long row of buttons to reveal the ugly bulge of flesh coloured bandages, unwinding the roll slowly when his shirt dropped to bunch around his waist. The weight shifted, and he couldn't help a soft sigh of relief as the pressure diminished, though he sighed when he finally sat topless, eyes pointedly avoiding his chest.

Ugly raw spots littered the soft skin beneath his arms, chafed open by the constant rub and shift of the bandages, ribs yellowed with old bruises.

“Just as I feared. I can give you a salve for the rash, and I recommend not binding for a few days to give your chest some time to heal.” He went over to the counter and put a small amount of lotion on a q-tip and rather than apply it himself he handed it to Oswald. “Make sure you get under your arm where the chafing is the worst.”

He nodded, happy to do it himself. With a wrinkle of his nose, he gently shifted the left side of his chest with his palm, sighing softly as he applied the cool salve, having mixed feelings regarding the doctor's advice. The action was repeated to the other side, and he sat still once more, absentmindedly holding his chest up in both hands.

“You can cover up again,” he replied, throwing the ace bandages away. “Now, have you considered testosterone, or top surgery at this time?”

“Yes,” he said, taking a breath. “I don't want to keep looking at these,” he specified, hands shaking the adipose on his chest as though it were not attached.

With an uncomfortable shift, he buttoned his top, disliking the sensation of bare fabric against his nipples. “How... do I get testosterone?” He asked, unsure how the process worked.

“It's a prescription and one that can be obtained easily. We can begin as early as today if it is something you wish to do.”

Oswald's eyes lit up.

“Really? It's that easy? he asked, eyebrows raised.

“Yes, Mr Cobblepot. There is a little pamphlet about testosterone here for you. We have a pill or an injection, but I'll give you a few minutes to read over the material.”

“Thank you...” he murmured, shifting to take it between two fingers. The pros and cons of each were displayed with an easy to read chart that explained the dosage and side effects in clear terms.

It seemed the pill was less expensive and easier to take but under-delivered in terms of effect and it had to be taken a certain way or it would do nothing. Oswald wasn't certain he liked the idea of sticking himself every three to seven days, but the promise of results was enough to disregard the discomfort.

“Could I try the injection, please?” he asked softly, mind racing with long repressed daydreams of a more respectable lower voice, sharper features, the potential to be taken seriously as a man!

“Of course, Mr Cobblepot. Give me a few moments to go get the injection and set up your prescription and we’ll be right as rain~”

“Thank you!” He beamed, kicking his feet back and forth happily when he was left alone in the examination room. It was monumental, suddenly having this intimate care thrust upon him so generously. He felt as though he were a baby bird, finally ready to spread his wings in the wind and soar.

After ten minutes the doctor returned with a few packages of plastic, of what looked to be clothing, and a small box. “This is the first dose, 25ml. Overtime we will up the dosage, but I wish to start small as we don't know what side effects you'll have. Please pull down your pants just a bit. I need access to your upper thigh.”

Oswald nodded, for once unbothered by the request to expose himself. Quickly, he unbuttoned his trousers and wiggled them down his hips to reveal the soft new boxer-briefs Butch had urged him to purchase when they were out buying clothes, as they were his favourite brand. They were very comfortable around the width of his hips and girth of his thighs.

He sat with nervous excitement as the doctor prepared the syringe, watching carefully.

He sanitized the area and barely gave him a moment’s pause before he stuck the long needle deep into the thigh to administer the testosterone. Once done he wiped the area and put a small bandage on. “All done, Oswald.”

The alcohol wipe was cool against the hairless surface of his thigh, and a soft gasp was the only reaction there was time for as the needle disappeared and then it was done. Almost instantly he felt confident, masculine- though he knew it was simply the buzz of serotonin in his brain giving him an extra push. He shimmied back into his trousers with a thrilled expression, uncaring even as his chest shifted with the movement.

“Thank you!”

The doctor smiled, glad to see as patient so happy. “I'll make an appointment for you next week, but you can do the injections after that at home. It was good to see you, Mr Cobblepot, tell Miss Mooney that my wife and I shall be by the club next Thursday.”

He nodded vigorously, coming to stand. The injection site throbbed slightly, but only served as a pleasant reminder of his first stride toward being happy with himself.

Taking the packaged binders in hand, he offered another charmingly innocent smile and slipped out into the waiting room to find Butch.

Butch was reading a magazine in the waiting room and stood once he spotted Oswald. “All good, kid?”

“Yup!” He replied, rather wishing he could slip into the new, stretchy looking tank top immediately, but the doctor was right, the damage to his skin needed time to heal. For now, he simply grinned down at the plastic bag, imagining what his chest might look like in contrast to the job done with the subpar bandages.

“Then let’s get back, I’m sure Fish would like to know what we’ve been up to~” he chuckled, escorting the young man from the clinic. Once they were in the car Butch began driving back to the club in silence. After a few minutes he murmured, “Hey kid, can I ask you something?”

“Depends on the question”, he replied, eyeing the other man curiously.

He hesitated for a moment, eyes firmly on the road. “Why do you want to be a guy? Is it like a gay thing? Or... you just like how you look in suits?”

An abused chuckle vibrated at Oswald's lips. “No, it isn't a gay thing... At least I don't think so. I haven't really gotten around to sorting out that part,” he admitted, comfortable talking to the big mobster. “Think of it like this... If you woke up tomorrow morning in the body of a woman how would you feel?”

His face went through several emotions rather rapidly, settling in the end on a smirk. “Depends, am I alone~” he grinned lasciviously.

“Okay after that part, you pervert,” he snorted “You have to just live with being a woman every single day, how does that sound?”

He frowned, comprehension dawning on his face. “Ah, got it.”

“So, take that general feeling and pretend that you've felt that way pretty much every day of your life... Does it make sense?” he asked earnestly, hoping that the other man understood.

He nodded. “That sounds like a shit existence, Oswald, I'm sorry.”

“Thanks,” he breathed with a half-smile. “I think it's getting better though. I'm so lucky to have met Miss Mooney...” he sighed happily.

He smirked softly. “Yeah Miss Mooney is a real lady, eh~?”

“She's so beautiful...” he agreed. Beautiful in a way that he had never been, and never really would be, but he admired it all the same, as one might admire a shining gem.

He raised a brow, chuckling softly as he pulled up next to the club. “Get out, loverboy~”

“Don't call me that!” he protested with a thinly concealed smile, secretly delighted as he climbed out of the passenger's seat.

Butch laughed as they entered the club. Fish greeted them with a smile and a kiss. “How are my favourite boys doing?”

“Very good, Miss Mooney,” he chirped in reply, still surging with hopeful confidence.

“Did you get everything you needed, Oswald? They were helpful, I trust?” The way she spoke carried a thinly concealed threat; if they had mistreated her boy there would be hell to pay.

“Yes, they were very kind, I-” his voice dropped to more of a whisper, “I received my first shot, and they gave me these tops to bind properly with...”

She smiled and pet his hair. “I'm glad, sweet boy. You made another appointment, I trust?”

He nodded, melting beneath her touch- everything seemed so wonderful and right “Then I have to start doing it myself.”

“Perfect,” she replied, voice like melted chocolate. “I want you to have everything you need, Oswald.”

“I cannot thank you enough Miss Mooney,” he breathed, utterly grateful.

“Play something for me, dearest, I can't stand the sound of silence.”

“Of course!” He replied, scurrying to the piano to fill the club with a happy tune.

The club bustled and continued its business through the night, Fish flittering in and out as she attended to business. Soon it was closing time and with a wave of her hand she dismissed Oswald.

Pressing a kiss to her knuckles he bowed and took his leave, practically running home to tell his mother about his good fortune.

“The woman who runs the club is so good to me mother, she's fronted the cost of all the medical bills!” He explained, showing her the sleek new method of binding he had been given.

“Just don't forget that no woman will ever love you as much as your mother”, she cooed, stroking the sides of his face.

Hidden in his room, Oswald could not resist slipping on the new binder, wincing slightly as the stretchy fabric stuck to the chafed spots on his skin. The pressure was even, and with a small amount of adjustment he was astonished to find his chest was almost entirely flat. Rejoicing quietly, he slipped the garment back off and slid into bed, lulled to sleep with a wide smile painted across his cheeks.

 

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**Notes for the Chapter:**

> I'm going to try to post chapters weekly! I'm so happy with all the positive feedback the first chapter had.


	3. Chapter 3

**Summary for the Chapter:**

> As Oswald begins to learn and grow within himself he is also ascending the ranks of Fish Mooney's gang.

Over the next few weeks Oswald settled into his role at Fish Mooney's club. He played the piano nightly. By day, he began serving as Fish’s errand boy, dropping off packages to local bosses, delivering a letter, or note, here and there. He was not privy to much of the operation, but he was slowly earning more and more trust.

His suits were finished within a week or so, and delivered to the club; Fish having presented them with a flourish. Oswald's delight tickled her pink, and for the first time in a long time she felt a warmth in the pit of her stomach, a tenderness she hadn't known she was capable of feeling again. He was full of praise, and seemed to take every kindness from her as if it were divinely given. He gave her a power she desperately craved, and in return she granted him privilege few had. Slowly it was becoming difficult to associate Fish Mooney without her little toady Oswald Cobblepot.

When he arrived for his shift that evening Fish called him to her side.  
He had begun administering his shot on his own, and after several agonizing days of waiting he finally began to see the beginnings of changes; though not all were positive. He had become increasingly sweaty, skin objecting to the change by breaking out over his cheeks and forehead.

“Good evening Miss Mooney,” he smiled timidly, feeling rather tired of all the people.

"I have to go run an errand later, would you like to join me? Hold my umbrella as it were?"  
Oswald could only assume this was not an ordinary errand, and nodded with a mischievous smile. "I would like that very much, Miss Mooney," he squeaked, voice catching on itself.

A burly man in a leather jacket entered the club, giving a cheeky salute to the bartender before swaggering up to Fish. "Harvey~!" she greeted with a smile, kissing his scruffy cheek.

"To what do I owe the pleasure?"

"Looking for a druggie, Fish, name's Jacob Logue."

She shrugged elegantly. "I don't know, Harv, why do you want to know where a little punk gets off to?"

"Word is he had info on what happened to Maroni's shipment."

"I say let it die, Harvey. If Maroni wanted him he'd have him. It's probably a dead end."

He sighed, and took the offered drink from the bar. "Yeah, that's what I told Essen, but she said to come ask~ It's always good to see your pretty face."

"Your welcome to gaze upon it whenever you'd like.~" she smiled, dark eyes glittering, hand twirling in an elegant arc.

He finished his drink with a single swallow and set the glass on the bar. "You take care of yourself, Fish."

"Likewise," she replied smoothly, lilting voice like a gentle caress. She had that detective wrapped around her finger. With a smile and a bow of his head he left, no investigation, no more questions.

Oswald watched in awe from his as she swayed and laughed, playing the detective like a fiddle as she lied to his face.

"Miss Mooney you are so devious~" he smirked softly, resting his chin against her shoulder.

She pet his cheek, nails scraping against his jaw. "Remember that a woman is a dangerous thing, Oswald~"

"Yes ma'am,” he purred, nuzzling against her warm hand with a toothy smile. His infatuation with the powerful woman only swelled with each passing day, utterly devoted to his beautiful goddess.

"A women is to be treated like a loaded gun~"

"Too right you are, my sweet boy. Now, let us run that little errand~" Fish allowed Butch to drive, Oswald sitting in the back with her. "Now, tell me, Oswald, how are you feeling?"

"Not... terrible", he admitted, wiping at his forehead with a quick swipe of the sleeve. Sitting with his legs too close together made him wince, finding a particularly intimate part of his anatomy growing increasingly tender with each passing day. The potholes were not helping. "I keep reminding myself that it has to even out at some point", he sighed, picking at the edge of his binder through the fabric of his button up.

"I don’t know what you’re going through, Oswald, but you let me know if there’s anything you need, understand?”

He nodded, tips of his ears growing pink as his mind drifted to another startling issue; his nonexistent libido was running absolutely wild.

But Miss Mooney would never do that. What that entailed he wasn't precisely certain, but as he'd slowly allowed himself the pleasure of learning his changing body, he had begun to fantasize about what it would be like to share such sensation with another; this was a dream that plagued him both in the waking and sleeping hours.

"I'll let you know if I think of anything". He smiled

"Good boy~" The car stopped and Butch came around to let Fish out. They had come to a small laundromat and Fish strode in with a grin, going immediately out back. She knew she would be followed by her boys and had not a care in the world. There was a long table in the back, money out and being counted meticulously by several young men.

Oswald followed behind her closely, keeping his eyes and ears open as they slipped into the back room.

She began to talk with a well dressed man, a dangerous glint in his eyes. "Miss Mooney, you know I have been on time with my dues~"

She sneered, hand coming up to grip the oily man's cheek. "Don't lie to me."

The movement in the room continued, the counters not stopping to assist the manager as their true boss assaulted him.

"Miss...Miss Mooney, please...I...I have the money."

"My money, of which you were half a grand short this month. You're not trying to cheat me, are you, Harold?"

"No-No..." She held out her hand, Butch handing her a bat. "Pl-Please Miss Mooney, I'll get you your money, I swear!"

Oswald watched in awe, determined that someday he would be looked upon with such trembling fear and respect. As her manicured fingers closed around the metal he bit his lower lip, watching in quiet anticipation.

"I would love to believe you, but I am worried about your sincerity." She let the bat fly, hitting him square in the side. He went down with a shout, curling in on himself.

Oswald flinched at the hollow metallic sound, but did not look away as his goddess delivered her wrath.

She delivered a few more whacks for good measure and then handed the bat back to Butch. "My money, by tomorrow." She turned on her heels and walked from the laundromat, gesturing for Oswald to follow.

As a crimson stain slowly spread across the linoleum, Oswald finally tore his eyes away, following after her with quick strides, sneering at the blubbering man on the floor as they exited.

They got back into the car and Fish grinned as she sat back on the plush leather seats.

"You are so beautiful when you're reminding people who is in charge~" he said, in awe of her yet again. Climbing in beside her, he stretched his limbs, settling back with a smile.  
She grinned as the car began to drive away. "Sometimes, Oswald, people need a little reminding. You hope all the sheep flock correctly, but sometimes they need a firm hand to get them back in line~"

He nodded, soaking up every word.

Once they got to the club Fish did something she had never done before, invited Oswald out back to the private offices and rooms.

Feeling honoured, he stuck close to her, examining the ritzy decor with interest.  
She opened the door to what looked to be a small apartment. Once in she sat down on the bed and quickly took her shoes off with a wince.

Oswald knelt before her, taking a foot in hand gently, as he had often done for his mother. "Allow me, Miss Mooney..." he said softly, looking up at her earnestly as he squeezed the arch of her foot.

She grinned, quite impressed with initiative, and sat back. "Thank you, sweet boy. You've lovely hands."

He had always found them short and ugly, piano had been a challenge to take up without the advantage of long fingers. Still he smiled, heart fuzzy and warm as he rubbed Fish's feet, looking up at her with devotion.

She allowed him to pamper her after a long day, talking to him of inane things such as fashion, alcohol, and deeper things like beauty, murder, and mothers. After a while she patted the space beside her, wanting to lie down.

Heart fluttering, he perched on the end of the bed reverently, speckled cheeks flushed.  
"Lay down, or get out, you're looming," she murmured, dark eyes falling shut.

"Yes ma'am", he squeaked, cursing inwardly as his voice cracked in betrayal. Stomach filled with butterflies, he lay beside the beautiful woman at a respectful distance.

Fish rested her head against the pillow, fingers lightly playing along the plains of Oswald's back. "You did well today, Oswald.”

Oswald sighed softly in contentment, heart thudding lightly in his chest as her fingertips roamed gently. "Thank you Miss Mooney" he breathed, letting his eyes fall shut for just a moment to focus on the touch.

Her long nails scratched along his back and shoulders, trailing down before her hand fell to rest on his side.

It was not at all unpleasant, and he found himself longing for the touch. "That felt very nice..." he murmured softly in gratitude, suddenly wishing he had taken off his suit jacket.  
It was not long before Fish slipped into a light sleep, hand resting on his side. She was confident the boy had enough sense not to be there in the morning and to not make a fuss.  
Oswald lay there quietly for a few moments more, savoring the strange gift of intimacy he had been given, then slipped away to return home.

Over the subsequent weeks he found himself occasionally invited into that secret realm of closeness; Fish would cup his cheeks, stroke his hair, and scratch his back, then he would be gone in the morning despite the strong urge to cuddle closer and fall asleep beside her.

It was late in the evening when he finished his performance, wandering to the bar for a glass of water and a proper drink. It was growing more difficult to maintain his confidence with the increasing changes in himself and he felt rather ugly, choosing to sit at the end of the bar away from the crowd.

Fish laid on her bed, feeling quite confident that her plan was coming along nicely. Falcones empire would come tumbling down by her hand or she would raze the city to the ground and salt the earth.

Still, as she shifted in her bed she felt a distinct unease with herself. How much did a person have to blacken their soul in order to achieve revenge? To what depths must they sink to gain what they desire. Not for the first time she wished that she could simply fall asleep, let the exhaustion plaguing her pull her down at last.

When her thoughts turned maudlin like this there was a simple solution, she called Butch in, covering herself with her blanket. "Darling, I need a drink, and is Oswald still here?"

"Yeah, he's sitting at the bar. I'll go get him."

"Thank you. Did Dimitri sneak out the back?"

"As always~" He replied with a smile, going to fetch the boy. "Hey Oswald, Fish wants to see you out back."

Oswald smiled brightly, drawn from his melancholy at the mention of his goddess. "Excellent, I will be there right away,” he said, tipping back the rest of his drink and standing to order Fish's favourite cocktail.

Drink in hand, he made his way back through the now-familiar hallway and knocked twice on the door.

"Come in, sweet boy, " Fish crooned from the other side. She was lying beneath her covers which was quite unusual for their encounters and as she sat up to take the drink from him they slipped just a bit to reveal a soft naked shoulder. The long line of her neck was elegant and tantalising as she surveyed her dear boy, inviting him to sit by patting the covers.

"You look warm, Oswald, get more comfortable."  
The lights were dim, a soft record playing in the corner. He stepped into the room, making his way to Fish's side with a fluttering stomach as his eyes took in her soft caramel skin, breath hitching as he realized she lay bare beneath the sheets.

"Comfortable?" he asked, managing to keep his voice even. Surely this was not what his libido-wrecked mind screamed that it must be. Why would Fish want to sleep with him? How would he even-?

He seated himself on the end of the bed, shrugging off his suit jacket with a quiet sigh of relief; he had been rather warm. Twin patches of red hung over his cheeks as he lay the article flat beside him, a warm throb settling between his legs as the scene settled into his brain.

Fish finished her drink and set the glass down on the bedside table. "You have been going through quite a few changes these past couple of months, I've noticed. How are you feeling?" She lied back down, blankets covering her once more.

Oswald exhaled heavily. "In the grand scheme of things I am feeling better, I think... though I confess I am beginning to grow unfamiliar with myself.”

His voice had slowly burrowed deeper into his throat, though it cracked mercilessly at inopportune moments. Then there was the hair. Oswald had always been a relatively hairless individual, and though the new growth was soft and fine, it was in places unaccustomed to the prickly intrusion.

Then there was... that.

The persistent throbbing between his legs, the sensitive bud swelling and changing slowly, tugging at his guts in an unfamiliar way. Masturbation was never something Oswald favored, but lately he had taken to plunging his hand between his legs at night, hidden safely beneath the sheets as he explored the new sensations of pleasure.

"And this~" she asked, fingers drumming along his back, nails scraping against the binder that lied beneath his shirt. "Have you thought about surgery?"

He arched his back slightly at the touch. "Yes, I would like that very much..." Oswald admitted. The binders were nice, but they still had to be removed at night, and had a tendency to pinch and ride up over the course of the day.

"All right, I'll look into it. My plans are all falling into place, Oswald, and once I rule Gotham you, Butch, and I will want for nothing. I'll need someone to run this club and this territory..." She murmured, hand trailing under his shirt to scratch the warm skin of his back.

Oswald sighed softly, shifting his legs apart and leaning back a bit into the touch. "I cannot wait, my queen."

"You wish to do that for me? Run my club and oversee these territories~?"

"I would be honoured, Miss Mooney" He replied with a wide, devious smile. "Anything for you~"

"Good boy," she murmured, voice soft and far too close. "I knew I could count on you Oswald."

The young man trembled, a powerful tingle running down the length of his spine. "I owe everything to you..." he breathed, air about him feeling hot and sticky. "I would happily rule on your behalf."

She nodded, mind at ease once more. Oswald was good for that, a simple minion to stroke the ego, a marvellous pet. He kept things in perspective for her and she was grateful for that. Soon their conversation slipped into the mundane and she fell asleep listening to his low hushed voice.

Almost bitterly, Oswald slipped back home, dreams filled with heat and skin on skin. He awoke sweaty and irritable, pointedly ignoring the wetness that clung between his legs as he dressed.

When he arrived for work Butch greeted him with a soft smirk. "Oswald, I think it's time you and I had a little talk. I think of you like an awkward little brother, and as a brother I gotta tell you that little moustache you're growing has got to go. You look like you're 14." He wrapped an arm around him leading him to the rooms out back.

Oswald sputtered in protest from his place firmly locked beneath Butch's arm. "No, wait, it doesn't look that bad!" He protested weakly, oddly sentimental about the sad, scraggly excuse for facial hair.

Butch gave him a look and pulled him along the hall with ease. "We can't have 14 year olds working in the club Ozzie~ it's got to go."

He stuck his lower lip out in a pout, as though that would somehow keep him from looking fourteen. "Fine..."

"All right, so I'm gonna teach you how to shave. Real men keep a nice clean face, looks professional, like you mean business. " He escorted Oswald into the bathroom where he kept a small kit of things for personal hygiene. He took out a razor and cream and began to lather his jaw and cheeks. "Just do as I do, okay~"

Endeared, Oswald obeyed, mimicking the other man in what was surely a 'father-son' moment as he spread the shaving cream over his sad excuse for a mustache, spreading it out as Butch did.  
"You want to go with the hair, that way you don't get stubble, or ingrown hairs." He pulled the razor down his cheek smoothly, wetting it before doing the same thing again and again. He reached into his bag once more and pulled out a razor for Oswald.

Holding it carefully between his fingers as though it were dangerous, Oswald wet the razor and brought it up to his face, successfully shaving a thin line away. With a faint smile, he continued, wincing slightly when his confidence betrayed him and he nicked the crease of his cheek. "Ow..."

Butch looked down with a roll of his eyes. "Happens everyone's first couple of times. Whatever you do don't put a bandage on it. You'll look even more like a child."

Oswald frowned as a pinprick of blood formed, stinging as he continued. "So I'm just supposed to bleed everywhere, check" he grumbled, managing to keep from doing it again.

He chuckled and finished his own face, leaning over the sink to rinse it. "And that's it~"

Oswald did the same, quietly mourning the loss of his facial hair but unable to disagree with Butch- he did look much more professional. Flashing himself a smile, he tilted his head to the side, pleased to notice that his jawline seemed a bit thinner, more defined.

"Thanks Butch", he said, bumping the larger man with his shoulder in playful thanks.

"You're welcome kid, I expect you to keep it up. Oh, and before I forget..." He reached into his bag and took out one of his deodorants, tossing it to him lightly. "You need to cover up like a man now~ because you stink like one."

Oswald snatched it out of the air with a giddy smile. Being treated like one of the boys felt so good . "You're one to talk, I know what you did in the end stall last week" he joked, taking a moment to apply the extra strength deodorant; he'd never really needed it before, but had become increasingly pungent as his body chemistry shifted.

"Charming, Oswald~" he laughed, shoving him lightly

"You started it-" Oswald grunted, stumbling on one foot for a moment, chuckling freely. He brought a hand up to his cheek, rubbing absentmindedly as he admired the smooth feeling.

"Now you can face Fish~" he said with a smile.

Oswald flushed faintly, turning to look up at the other man. "Speaking of Fish... You'll never believe it, Butch last night she invited me back to her room and she was naked." He spoke in the sort of scandalous half-whisper common in stories shared between friends.

Butch looked at him queerly with a raised brow. "You keep that between you and Fish, understand. It would be in your best interest, Oswald, to pretend nothing like that happens during the day."  
"I know that- I just... I wanted to ask you because you know her..." the small man replied quickly, fidgeting with his collar. "She... she would never be with someone like me, would she?"

He sounded melancholy, but as though he had already accepted this truth.

Butch looked at him with a pitying expression. "You're not her usual type, kid, no."

"I figured" he mustered a sad smile, "I just had to be sure". With that, he slipped out, trying to ignore the cloud of disappointment settling over him as he sat up at the piano to begin his set.

Fish watched him from her table, a smile about her lips. He was a lovely creature, pale and small. He was certainly very taken with her, and devotion was something she valued highly.

It was quite a shame he wasn't more useful.

As he played a sweet, sad tune the young man forced his gaze away from his goddess, instead observing the patrons. There were a few that caught his eye- some male, some female- each with their own beauty about them.

After the show, when Oswald was getting his customary drink a young blonde shimmied into the stool next to him, elbows on the bartop as she slouched in her seat . "You played so good~" she cooed, the tips of her fingers playing with the fabric of his sleeve.

Oswald looked up at the sound of her approach, rather taken aback by the sudden proximity between them as he sipped his drink. "Thank you", he smiled nervously, studying her face with a curious interest as he gently withdrew his sleeve. His hand, however, returned to the same place as before and he allowed her to curiously trace each of his short fingers, admiring the way she smiled to herself in amusement.

"Are you enjoying yourself?" He asked curiously, quickly ordering a second drink for himself as she somehow moved even closer.

"Yes~ I really liked your playing, you were very handsome up on stage," she whispered, leaning close.

His skin tingled in a way that was entirely pleasant as her breath ghosted over his ear.

Straightening up, he smiled more widely, admiring the way her long hair fell in cascades over her shoulders.

"You think I a handsome?" he asked, buzzed with a sudden confidence as he turned to face her. "This coming from someone as lovely as you, I am honoured".

She giggled, swaying dangerously in her chair. "Nonsense~ The way you played, I bet these fingers are very agile," she smirked eyes glittering in the dim light of the club.

"I have practiced for many years, they've become quite fast" he replied, intrigued by the way this woman was speaking to him.

She grinned, licking her lips. "Oh I'll bet~" She leaned over and kissed his cheek, seeming to ignore the slight sheen of sweat on his skin.

Oswald flushed faintly, keenly aware of how close the woman was. "What is your name?" he asked, finishing his drink.

"Tanya," she purred. "You're Oswald, right?"

"That's me" he replied in what he hoped was a suave manner. Nothing about her appearance particularly appealed to him, but her undivided attention was doing wonders for his abused self-esteem.

"Do you wanna go out back~?" She asked softly, lips brushing against his ear.

"Really?" his breath hitched, stomach tightening with a warm throb. "Yes, yes let's", he added, standing quickly as he spot Fish watching from afar.

Fish's eyes tracked the pair and a slow smirk spread across her lips. The boy seemed to be coming into his own.

She gave him a casual wave from afar, a blessing of sorts, as the girl pulled him near the bathrooms.

Flushing deeply as Fish disappeared from his line of view, he turned to face the woman. She was close enough to feel the heat of her body, a few inches taller than Oswald.

She tilted his chin back and kissed him briefly, hands caressing his sides and chest.

Oswald shied away from the touch, but simultaneously pressed his jaw forward to encourage the kiss, stomach turning with nervous arousal.

She kissed down his jaw, hand cupping the front of his trousers.

"E-Easy!" He gasped softly, jumping back.

"Oswald, why so jumpy~?" she purred. "I promise I'll make you feel good. "

"I..." He hadn't expected anything to happen quite so fast, what was he supposed to say?

"Thirty for my hand, fifty for my mouth, and a hundred by the hour for anything else," she murmured, hand trailing back between his legs.

A disappointed groan escaped his lips, and he wrenched himself away from her perfumed grasp. "There's been a misunderstanding..." he managed to grit out, disappearing from the hall to hide backstage, frustrated tears prickling at his eyes as he sunk down the wall in a shadowed corner, cursing his optimism.

When the girl came back without Oswald, Fish became more curious. She stood from her table and went out back, trying to find her sweet boy.

He re-emerged after a few moments, making his way back out to the bar before hiding in a corner booth alone away from the bustle of the night’s crowd. What had initially been a thrilling encounter left him with a sour feeling in his stomach, body aching and confused as he bitterly drowned his sorrows in sweet flavoured liquor.

After a few minutes Fish joined him, looking him over appraisingly. He had been crying, seemed to be trying to find solace in his drink. "There you are, Oswald."

"Hello Miss Mooney", he greeted stiffly, feeling irritable as the beautiful woman slid into the seat across from him.

"You seem upset, sugar. Tell mama all about it," she murmured, reaching out to touch his hand gently.

"A woman approached me at the bar and seemed very interested in me, but as luck would have it- she was a call girl", he replied bluntly, embarrassed and frustrated. He should have known a woman like that would not be truly interested in someone so short and sweaty.

She looked at him sympathetically. "That girl is of little consequence, Oswald."

"I know that ", he sighed, fingertips playing with the cool drops of condensation on his glass. "...But for a minute I actually thought about going with it anyway. That is, until I realized she was grabbing for something I didn't have, something I couldn't even begin to explain to my mother much less a prostitute!" He hissed quietly, eyes darting about for eavesdroppers. "I ran away like a coward".

"Ah, I understand." She nodded. "So here you are, burying your confusion and anger in bourbon? "

"I guess so, yes" Oswald muttered into his drink. He had never been attractive, it wasn't so much a blow to his ego as it was a torment to his mind.

"Oswald, why do you care about the opinions of a whore?"

"I don't! Not really, anyway… but I panicked", he groused, crunching on ice cubes. "What am I even supposed to do?", he queried with a mortified whisper, tongue loosened with liquor. "I don't have what anyone expects a man to have, I've never even gone down on anyone before!"

She chuckled softly, covering her mouth with her dainty hand. "Oswald...matters of the body, as with matters of the heart, are not things that can be rushed, sweet boy. When you find a nice person you'll come to understand that sex isn't just a man thrusting his penis into a woman. It's...much more than that. Trust me, sugar, you don't need a dick to make a lady feel good~"

Red faced, Oswald nodded. "I think I got ahead of myself..."

"What is it you want in a partner, Oswald? Did that girl even appeal to you?"

"Not really", he admit with a soft huff. "My mother always told me that life only gives you one great love... I guess maybe I always thought I'd know when I found them"

"Then there's no rush, love. You certainly won't find true love here of all places."

"I figured as much but-" he swallowed shyly, choosing his words with a nervous smirk "-my body craves company and it's rather maddening what a moment of positive attention will do to me".

She shrugged easily. "If it's just pleasure you want that can be gained easily enough. There are many people in the club who would not mind your company, or perhaps pay for it and with it their silence on your more sensitive secrets~?"

"I worry for my reaction", he mumbled, dismissing the conversation with a wave. "I think this was enough to let me know I'm not ready, not yet".

She reached over and laid a gentle hand on his.

He smiled, her skin was cool against his own. "Thank you for checking on me, I feel much better". He recalled what Butch had told him before, that he wasn't her usual type, but her attention was pleasant and welcome all the same.

"I'm glad, sweet boy, I do so hate to see you frown."

"You are too good to me Miss Mooney" he replied, kissing the top of her hand as he often did.

"Just remember how much your mama loves you, Oswald."

"I'm the luckiest boy in the world", he beamed.

She grinned, and finished her drink. "I'll see you tomorrow, Oswald~ I've another errand to run. You should get home and get some sleep. Tomorrow is going to be a looong day."

"Yes ma'am", he agreed, standing to press a kiss to her cheek before disappearing out the back entrance.

Gertrude greeted her dear son once he was home. "Oh Oswald...it is so late. These hours you keep, I worry about your health."

"I'm okay Mother", he smiled tiredly, holding her close in a tight embrace. "It will be worth it" Oswald assured her, pecking her gently. "You shouldn't stay up so late waiting for me, though"

"A mother worries," she cooed, holding his dear sweet handsome face. "You were with a woman~?" she asked, stepping back with a small frown.

"What? Of course not mother, I don't know any women..." he said, feeling a bit prickly. Had she smelled the whore's perfume or was it Fish? Either way, she had no reason to fuss, in his opinion.

"Cheap perfume and liquor, I know the smell," she breathed. "You were off with some painted lady."

Oswald laughed softly. "I work at a nightclub mother, everyone smells like liquor and cheap perfume"

She clucked her tongue and smiled at him. "As long as I am the only woman in your life, my darling. I am happy~"

"Always, mother", he promised, kissing both of her hands before slipping into his bedroom.

"Such a good boy," she murmured, moving to her own bedroom to retire for the night.

 

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	4. Chapter 4

**Summary for the Chapter:**

> Oswald learns that not everyone is as accepting as his family.

**Notes for the Chapter:**

> Warning: transphobia, dead-naming, and general horrible behaviour in this chapter.

Two months later, Oswald arrived at the small clinic for a regularly scheduled check up, allowing the kind doctor to weigh him and ask him various questions about his appetite and changing body.

Swallowing nervously as he removed his top, Oswald once again voiced his desire to have his chest fixed. The binders he had been provided with did wonders, but they were constricting, and still had to be removed at night.

"I was hoping you could help me find a surgeon, I'm getting tired of the routine..." he nodded to the binder he had wrestled off, jaw tight as the doctor checked his skin and ribcage.

The doctor looked Oswald over, nodding as he scribbled in his chart. "You've reacted well to the testosterone, by my estimation. If you're certain the surgery is what you want I know of a few cosmetic surgeons of renown in the area. I can refer you to them," he replied. "He'll want to do a referral first, before anything is finalised as this is more permanent than the testosterone."

"Yes, of course", the young man nodded, slipping back into his clothes when the physician was finished. Though a nervousness clung to the pit if his stomach, he was outwardly confident.

"I'll make the referral, and you should be able to call for an appointment before the end of the day, Mr Cobblepot."

"I appreciate the assistance." He nodded, finishing up the buttons on his shirt and smoothing his hair. "Thank you."

"Of course, and please give Miss Mooney my regards?"

The next few days went by in a blur, appointments were made, Fish's full support granted with that warm twinkling smile. He had performed admirably in the mounting war with Maroni, and Fish could not be happier to grant this favour for her little man.

When Oswald arrived for his consultation with the surgeon he was in high spirits, having been fantasizing for several days about the freedom he would soon have. Soon he would be rid of the useless additions to his chest entirely, no more tight binders and itchy heat rash!

He stepped into the waiting room and checked in with the receptionist, sitting tall in the corner with a small smile clinging to his lips as he await the call of his name.

The surgeon came out and surveyed the waiting room. When his eyes came to rest upon Oswald his nose scrunched up as if he smelled something unpleasant. "Olivia Kapelput?"

Oswald flinched, eyes darting around the room nervously. No one seemed to be paying any attention, so he stood briskly, hoping to correct the doctor quickly in private.

"I'm sorry, I believe there's been a clerical error...my name is Oswald, Oswald Cobblepot,” he murmured between tightly grit teeth as he pointed to the name on the file.

Why was his old name even on the paperwork? He had to wonder, brow furrowing anxiously.

"This was the name on your original medical files, and your social. If you wish it changed you'll have to file with City Hall." He walked away, expecting Oswald to follow him through the winding halls of the office.

He opened his mouth, then shut it again, following mutely as his nervousness increased. This man did not seem as kind nor open minded as the physician he had been meeting with previously.

The doctor opened a sterile looking office and gestured for Oswald to sit before a deep mahogany desk. "So, what is it you are looking for?"

Seated, he felt quite small, fidgeting with the hem of his shirt tail anxiously as he spoke. His manner of speech was carefully selected and metered without giving away his nervousness entirely.

"Dr. Stevens informed me that you are the most qualified surgeon in Gotham to perform the procedure to alleviate the side effects of my... gynecomastia." A word that his previous doctor had used, a common side effect of hormonal imbalance in men; technically this could be applied to Oswald's situation, though a stretch. It certainly felt more comfortable to pretend it was an ordinary problem for an ordinary man.

The surgeons eyes narrowed. "Gynecomastia is a problem men face. A breast reduction or mastectomy would be most appropriate for someone like you," he answered with an air of finality, folding his hands on top of his desk

"It's the same thing, isn't it?" he replied, gritting his teeth.

"Not at all. One is a hormone imbalance found in men, and the other two surgeries are performed on women for any number of reasons."

"The important thing being that the breast tissue is removed,” he nearly hissed, rage slowly boiling within him.

Anger was not an emotion that Oswald was familiar with, but the quantity of items that piqued his ire seemed to increase with every passing day, and though he was attempting to remain passive, he rather wished to hit the dismissive man in the face.

"Have you thought about your future Miss Kapulput? Any husband you have will want children and if you get rid of your breast tissue now it will complicate a pregnancy exponentially."

 

"Mr. Cobblepot. Please. " he insisted, voice tight like the poorly tuned strings of an old violin, threatening to snap at any moment. "I have no plans or desires for children or having breasts any longer, so if you could please just get on with the evaluation..."

"Your primary care physician wrote that you have been on testosterone less than a year..."

"And?" Oswald prompted, feeling quite fed up with the man already. Why did it matter to him, he wasn't the one stuck with breasts!

The doctor stood, hands clasped behind his back. He rounded his desk and came to stand behind Oswald, hands on his shoulders. "I think it would be best if I spoke with your mother and father. I'm just worried a girl of your age is not ready to make such an important and permanent decision."

Oswald clambered to his feet quickly, utterly enraged. "I am 26 years old, and perfectly capable of thinking for myself," he snarled, shoving the horrid man backwards hard for daring to insult him, to bait him, to stoke the flame inside him to a roar. Winding back, he punched him once, twice, then pulled back, shaking the pain from his knuckles with a low hiss, shouldering past the antagonist with a growl, slapping the file from his hands as he escaped the tiny room.

His ears buzzed, crimson with anger as he hurried down the hall and out the front door of the clinic. Everything after that was a blur, and he found himself back at the club, seeking Fish out with a numb glance.

Fish was surveying a small shipment of alcohol in the back and did not immediately see Oswald. It wasn't until she heard the stomping behind her that she turned and saw her sweet boy, red faced and trembling. It was a wonder the young man still had teeth from how tight his jaw was clenched. What caught her attention most were the shining tears trailing down his cheeks. She immediately stopped what she was doing and directed her attentions toward Oswald. "What happened?"

"The idiot surgeon wouldn't stop referring to my old name" he hissed, swiping at his cheeks. "Had the audacity to tell me I should come back with my parents to make such a decision."

She blinked, at first not understanding the audacity of anyone in the city not only undermining a member of the Falcone family gang, but also refusing them outright. That simply would not stand. A dangerous gleam overcame Fish's eye and she took his hand in hers. "Let mama take care of it, my sweet. I'm sorry you were disrespected."

"I attacked him,” he whispered. “It felt right.” His fists quivered at his sides, cheeks stained a dull pink. "He deserved it..."

She cupped his cheek, eyes warm as she regarded him. "I'll have one of the boys pick him up. We'll make this right"  
"He gets paid no matter what, I don’t understand why he had to humiliate me like that!" Oswald groused, leaning into her touch needily. Her touch was cool against the anger-scorched surface of his skin.

"Some people are addicted to power, Oswald. They seize it wherever they can."

He sulked bitterly, feeling utterly emasculated by the experience. "It was meant to be an easy appointment, now I've set myself back.. "

"I'm sorry, Oswald. I can offer a small resolution, though," she smirked.

He perked slightly, meeting her eyes. "That being...?"

She snapped her fingers, Butch coming to her side nearly in the instant. "Yes, Miss Mooney?" he asked with a smile.

"I want you to go pick someone up for me and bring them back here, no need to be gentle, just make sure you're subtle. Dr..." She looked to Oswald.

"Just look for a man with a couple of black eyes..." he said quietly "I can't seem to recall his name."

"Nice, kid," Butch muttered. “Where?”

Oswald sniffed, arms crossed defensively before himself. “The Gotham General,” he muttered.

"I'll take care of it, FIsh," Butch said with a shake of his head, moving to leave.

"Trust, Butch, Oswald. He may be a big man, but he's good at this sort of work."

"I believe that", he sighed, massaging his hand with a wince.

"Did you hurt yourself?"

"My form might have been off," he chuckled lamely, flexing his fingers. "I think I'll be okay."

She reached over the bar and grabbed some ice, putting it over his knuckles.

Oswald sighed quietly, appreciating the kindness. "Thank you..." he murmured, chest still tight with anger and upset at the situation.

Butch returned two hours later with a man carried over his shoulder. He carried him inside, his hands tied at the wrists, head hooded so that he could not see. "Outside?" he asked.

"Yes," Fish answered simply. She crooked two fingers, wanting Oswald to follow  
Curiosity and anger burning within him, Oswald rose, moving close to Fish's as he walked behind her.

Butch none to gently threw him to the ground. He then removed hood, watching as the surgeon looked at each person with varying degrees of horror.

Oswald stood over him with a mixed expression; anger, pity, disbelief. He didn't speak, simply watching to see what Fish had planned for the unfortunate wretch.

"What the hell?" The surgeon growled. "Miss Kapelput when I requested to speak to your parents..."

He was silenced by fish grabbing his cheeks with her nails. "Idiots would do well not to talk."

"There isn't anyone here by that name-" Oswald hissed, resisting the urge to kick him "- and these are not my parents"

Butch chuckled, looking to Oswald then back to the surgeon. "Yeah, no thank you "

The surgeon snarled. "What do you want?"

"My name is Oswald Cobblepot, and you would do well to remember that", he hissed in reply, stepping forward slightly in anger.

"Is this really because you want your boobs taken off?" He asked crudely, incredulous.

"Shut up!" Without a second thought, Oswald brought his foot back and kicked the man firmly in the chest with fury.

He fell back with a grunt. "Stupid queer."

"I said shut up!" Oswald shouted, fists balled angrily at his sides.

Fish put a hand on his shoulder, stilling the little bird a moment before she calmly turned to Butch. With a smirk about her lips she murmured, “Butch, take his fingers."

"Wait...no...no!"

"You took an oath to serve those who needed it most. You are not performing your job and so were going to take your ability to do so~"

Oswald's face was pink, nose upturned as he glared down at the horrid man. "Thank you Fish..." he murmured, moving to press a kiss to her cheek gratefully. To see her go to such lengths to see that the matter was resolved favorably only increased his devotion to her.

Butch stepped forward, pulling as switchblade from his pocket.

The surgeon coward, and tried to scurry away before Butch grabbed him by the scruff and began to lop off fingers one by one.

Oswald clung to Fish's side, chin pressed against her shoulder as he watched in mixed horror and awe of the gruesome scene. She allowed him to cling to her for a moment before stepping away, forcing him to stand on his own two feet. So he watched as each digit was severed amongst the screams of the impudent surgeon, blood smeared in a terrific mess about the scene.

Fish smirked as the job was done. "Take him home Butch. He should be able to patch himself up,'" she replied cruelly.

In an act that surprised himself yet felt entirely satisfying, Oswald spat on the man as he was ushered past, smirking at the pile of fingers with a racing heart.

Fish turned to him, surveying his reaction. "How are you, sweet boy?" Not everyone was cut out for the realities of this life.

"I feel... good," he smiled, looking rather devilish as he moved to pluck a bloodied finger from the ground, inspecting it with a toothy grin. Adrenaline thumped in his ears, entire frame feeling almost numb with shock, and yet he felt utterly powerful in that moment.

"I don't think he'll be forgetting my name any time soon".

She laughed. "No, I suspect not, Oswald~"

He turned to face Fish, discarding the finger as he looked up at her in adoration. "Thank you... I know you didn't need to go to the trouble"

"He didn’t just insult you, Oswald. Now we’ll need to find you a proper surgeon, but this might take a little while. Are you prepared to wait?"

He nodded firmly. "I will wait patiently for the right doctor to be located."

"Good boy," she cooed.

He pressed a kiss to her cheek and departed, tired and eager to return home to his mother, who was no doubt preparing something delightful for dinner.

Gertrude greeted her dear child with a gentle kiss. "How are you, my little love?"

He had been careful to freshen up before his return, and buried his face in the kindly woman's neck with a happy sigh, glad to be home.

"Wonderful, now," he said, nestling against her with a gentle arm about her waist. "My appointment went very well,” he lied, not wishing to worry her with anything unnecessary.

She cupped his now scruffy cheek and grinned. "Handsome boy~ my Oswald I'm so glad. I always worry about these "appointments". Doctors, you can't trust them."

Oswald's anger was entirely soothed by her gentle touch and soft, familiar voice. He smiled, leaning into her hand. "Don't worry Mother, I have people looking out for me"

She smiled lovingly. "You are my joy, Oswald, I am so glad you've found friends."

The young man had never made many lasting friends as a child, often settling for the faux friendships with characters on the pages of a book. Oswald wasn't entirely sure if friend was the correct word to describe Fish Mooney. Butch, perhaps, could be considered strictly a friend, but her...she was not unlike his own mother, kind and encouraging yet also something dark and alluring.

"I'm finally doing it Mom, I'm finally becoming something great," he smiled happily

"My son, important business man~" she cooed lovingly. Her precious child had brought her nothing but joy. It seemed the more he went through his personal transformation he was growing before her eyes into the spitting image of his father. She smiled with watery eyes and kissed his sweet forehead.

"I love you Mother", he whispered, holding her close once more as she gently caressed his face and hair, almost absentmindedly. "I'm going to be a great man, and I promise to always take care of you"

She smiled. "Of that, my little cobble pot I have no doubt." She pulled his hand to bring him beside her on the sofa. "You look so much like him now, Oswald..." she breathed.

"R-really?" His breath caught in his throat, instantly realizing whom she was referring to.

Oswald had never met his father, nor seen any photographs of his face, there were none to be found. Gertrud had told him since he was very little that his father had died when he was a baby, with only her stories and descriptions of him as a memory.

Gentle tears welled in the corners of his eyes as he beamed at her.

"So handsome you are," she murmured tearfully. "Just like your father"

He pressed a kiss gently to her lips, brushing a long curly strand of hair from her face. "That makes me so happy to hear you say," Oswald replied, holding one of her hands to run the tips of his fingers over the many rings she wore, a habit he'd picked up when he was little.

"I know that he isn't here now, but... I'm glad that I can remind you of him. I know it isn't the same but..." he trailed off, sharing a tender look with his beloved mother.

She had worked so hard to raise him entirely on her own and she was his entire world.

"You have always been my pride and joy, Oswald. More than enough for me. Your father is not with us, but I know he would be happy of the man you have become." She sniffled slightly, pulling a lacy kerchief from her sleeve to dab at her nose and eyes. "You are so good to your mother; I could not ask for a better son."

"I couldn't dream of having anyone else as my mother... you've done so much for me" he rubbed her knuckles gently. "When you found me in the bathroom earlier this year I was so afraid of what you might think of me and you... you never even bat an eye" he smiled through his own tears, chuckling softly at their weepy moment together. "I love you so much..."

"It is a mother's job to love their child without condition." She grabbed his hand in a gentle but firm grip, soft hand surprisingly strong. "I will always love you no matter what, Oswald. You could break my heart into a million pieces and it will always belong to you~"

As Oswald held her warm fingers in his own, he could not help but think back on the way Fish had shown that she loved him and held her tighter still. She didn't need to know about any of that, he was a pianist at the nightclub, that was all.

"I am so lucky to have a mother like you" he nodded, wiping an errant tear from his eye before resting his head on her shoulder tenderly.

"I am lucky," she breathed. "Would you read to me, Oswald?" Gertrude stood, making her way down the hall to her bedroom. "It helps me to sleep, knowing you are there."

"Of course, mother."

 

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	5. Chapter 5

**Summary for the Chapter:**

> Oswald gets some much needed mother/son time with Gertrude as he continues to become disillusioned with his position in Fish's gang.

As he continued to showcase his worth and earn valuable trust, Oswald transitioned from pianist, to errand boy, to umbrella boy- rising in the ranks of Gotham’s underworld with surprising ease; it was as though he were meant for this life all along. He was rarely seen absent from Fish’s side, always quietly absorbing information as he clutched her purse or poured another chilled glass of wine. It was easy to disregard him, but the observant young man was privy to some of the underworld’s most sensitive information.

Oswald’s tender self-esteem was fast rising, and after taking a month off to recover from his surgery the young man felt as though he was on top of the world as he strode into Fish Mooney’s nightclub once more, a confident smirk upon his lips as he strode through the early evening crowd, delighting still in the subtle shift of starched fabric over his bare chest. The body Oswald felt he deserved was nearly in his grasp, and thought there was still a gaping absence between his legs, it wasn’t as though he had any use for such an organ at the time being; there was no time for petty romance in the life of Oswald Cobblepot, such issues could be dealt with at a later time.

“There’s my sweet boy~”

The sweet honey of Fish’s voice called out to him from the end of the bar where his beautiful patron stood in a dazzling fitted dress with sequins that glittered in the low, smoky lights of the club. She was balanced on a pair of gold stilettos sharp as her winged eyeliner, and Oswald could not help but admire her beauty a moment before embracing her. “I had nearly forgotten how lovely you are~” he crooned, a twinkle in his eye as a smile cracked her taupe lips.

“Coming from a handsome little handful like you?” She laughed, a gentle hand trailing down his flat chest curiously, long manicured nails clicking softly against the onyx buttons of his shirt. “You look good, Oswald,” she praised, drawing a faint blush from his pale cheeks.

“I feel like a new man~” he chuckled, both laughing at their secret joke.

The recovery had been agonizing, and the scars were still deep and red, but when he had stood for the first time before the mirror alone without the thick, itchy bandages he finally felt as though he were seeing himself as he truly was; a man to be respected.

Though he still occasionally graced Fish Mooney’s nightclub with a performance, more often that not Oswald could be found close beside his patron as she dealt with her underlings. Tonight, it was a snivelling debtor, begging for more time to pay as he squirm beneath her unimpressed gaze. The foolish man seemed to think that because Carmine Falcone’s control over the territory was slipping he needn’t pay his debts, and Fish seemed almost bored as she held out her hand for the long metal baseball bat that Oswald held in his left hand, an ugly smirk upon his lips.

He watched with rapt attention as she raised the metal bat and brought it sharply down upon the idiot’s side several times, breaking various ribs as the cretin swore loudly that he’d pay. The first time that Oswald had witnessed such ‘negotiations’ it had left him with a twisted feeling in his stomach, but now he almost wished Fish would pass him the bat, let him take a swing for once.

“That’s what they always say~” she crooned, pressing the bloodied weapon back into her umbrella boy’s hand when she was finished. “I expect to see that money tomorrow, or the next time I see you, you won’t be walking away”. She dismissed him with a bored wave of her hand, turning to face Oswald as the injured man escaped down the alley. “You see Oswald, you can’t relax for a moment or these idiots think they can do whatever they want…” Fish tsked, sinking into a chair with a quiet groan. smiling as her darling umbrella boy offered her a glass of red wine. “Darling, my feet hurt”, she sighed, blinking up at Oswald expectantly.

With a nod of understanding, he knelt down beside her to carefully slide off her expensive heels, setting them off to the side as he took a foot in hand, rubbing gently. It was a common ritual between them, almost to be expected by now and yet Oswald felt a twinge of disappointment. His admiration for this woman had not waned in all the time that he had known her; she had unlocked something twisted and fiery within him that was aching to be released, but as he sat below her, fingers absently working, Oswald could not help but wonder if he was destined for more than umbrella boy- perhaps one day he would have someone to rub his feet.

Unaware of his musings, Fish sighed in contentment as Oswald got straight to work, slowly draining a very full glass of red wine. Her previous terms of endearment seemed to fall by the wayside of late; they used to be peppered into her speech so frequently, but now Fish seemed less easy to impress, entirely consumed by her aspirations to extend her reaches of power through Gotham.

Oswald bit his lower lip, continuing his work quietly as she enjoyed her drink, submerging himself wholly into a delightfully vivid daydream, one in which he was a trendy nightclub owner by day and a fearsome mobster by night. It brought a true smile to his face, imagining himself seated comfortably in the same dimly lit booth with a cold drink, warm hands rubbing his aching feet as he listened to an attractive singer croon for him onstage. Distracted, he pressed into a tender muscle much too hard and Fish hissed sharply, striking him in the face with the top of her foot as her leg spasmed forward.

Oswald recoiled, an inexplicable anger rising up within him as he was struck from his daydreams. He held a hand to his temple, jaw clenched tight as a flicker of malice burned dangerously in his eyes for just a moment before vanishing. "I'm sorry, I'll use less pressure," he murmured, quietly leaning back in to resume his work.

Much too proud to apologise, Fish merely nodded and held out her other foot. She did however lean over and stroked the side of his face in appreciation. "You're so good to me, Oswald."

There was a time when the boy would have pressed his face eagerly into her hand, grateful for any drop of kind affection she had for him. Now, he seemed prouder, chin simply tilting upward to meet her eyes as her manicured nails caressed the sharpened edge of his jaw.

"You've been good to me, Fish," he replied sincerely, fingers gentle against the tired arch of her foot. He could not deny that.

Pride swam in her gaze. She had moulded Oswald out of clay itself and here he sat before her a confident young man, secure in his skin. "You're done for the day, Oswald. Go visit your mother, I'm sure she misses you. Take her out somewhere special~" she said with a wink. Perhaps it was her way of apologising for her behaviour, or a reward for services rendered, or perhaps it was the first kind thing she had done just for the sake of doing it, small though it be.

Surprised, but no less grateful, Oswald rose to give her a small bow. "Thank you, I'm sure she will be quite happy to see me while the sun is still up" he laughed, straightening his tie.

Working for Fish meant that his hours of employment were sporadic, and more often than not he found himself creeping home in the wee hours of the morning. Occasionally, he would return to find his sweet mother asleep on the sofa, having waited for him to return home. Those nights, he would cover her with a blanket and curl up in the armchair adjacent before falling asleep.

Grateful for the free time, Oswald stopped by a nearby floral shop to purchase a bouquet for Gertrud before returning home.

Gertrude was dancing about the apartment, a large feather duster in hand. Her flowing lacy dress twirled around her as she spun and twisted, dusting all the pictures of her dear son, newly framed, and his little baby pictures. She hummed an Old World tune as she worked, not hearing Oswald enter.

Beaming brightly at the pleasant scene, Oswald watched her a moment with a smile before he quietly set the flowers down on the coffee table and slowly crept up behind her as she stretched to dust an overhead lamp. Sliding his hands over her eyes playfully, he whispered "Guess who~?"

Startled, her elbow shot out behind her with a shout, catching Oswald firmly in the stomach as she hurried to disentangle herself from the ‘attacker’ raising the feather duster high with wide eyes. "Oh Oswald I am so sorry...you gave me a scare." she gasped as she recognized her beloved son.

In hindsight, her reaction made perfect sense; Oswald could never fault his dear mother for anything. "It's alright Mother, I shouldn't have snuck up on you" he laughed with a wince, eying her choice of weapon with amusement. How he cherished her. "I've been given the rest of the day off, I wanted to surprise you" he explained, turning to procure the bouquet of roses with a flourish, beaming from ear to ear as he awaited her delight.  
Her eyes filled with tears and she immediately embraced him. "What a wonderful son I have. So good to think of his mother on his day off!" She kissed both his cheeks and then his forehead as she fussed over him happily. “How lucky I am to have such a sweet boy”.

His heart fluttered happily, wrapping his arms about her to lift her in a gentle spin. An added benefit of his transformation- everything seemed much lighter now than it had months before. Setting her down carefully, he revealed his next surprise with a wide smile. "I'd like to take you to dinner tonight, Ma" he declared, wallet fat with his hard earned pay. "Somewhere nice, I want you to get dressed up"

"Oswald~ you should be spending your money on yourself!”, the old woman tittered with poorly concealed excitement, patting and tugging at the velvet lapels of his suit jacket happily.

"I want to spend it on you, mother" he insisted happily, taking her hand to gently brush over her rings. Their quality of living had certainly increased since the day he became employed with Fish Mooney; Oswald was slowly replacing old appliances and rickety furniture with his savings, delighted to provide in a way that he had never been able before.

"You spoil your mother Oswald~" she grinned, finally moving away from him with a flourish of the old feather duster. "Give me some time to get ready and we will go out."

He watched as she disappeared into her room, a record softly scratching out a tune after a moment. Oswald could picture her seated before her old vanity in his mind’s eye, having watched her beauty routine often as a child. It took Gertrude an hour to get ready but when she finally emerged heavy kohl lined her eyes, a deep pink lipstick on her plush lips. Her golden curly locks were tied back, pearls pinned in to dazzle. Her dress was a pretty purple colour, accentuated by a white scarf around her throat. Gertrud had always been a beautiful woman, but there was very little excuse for her to dress up anymore.

Oswald was delighted, embracing her to press a kiss to her cheek. "Mother you are the most beautiful woman in the entire world" he praised, admiring her outfit with a bright smile. How lovely it was to see her so happy.

She grinned, absolutely jubilant. Her precious child was such a joy to her and looked so resplendent in his new finery. He seemed so confident now, truly at home in his skin. She cupped his cheek with a coo. "My son, the success. I am the envy of every mother in Gotham."

"I'm so happy to make you proud" he beamed, leaning into the touch with a flutter of his eyelashes. "We have reservations for a lovely place in downtown Gotham" he revealed, having called ahead while she was getting ready. As an extra touch, he had also procured a ride with a driver for the evening to transport them to and from their dinner, using a few of his connections through Fish.

"Downtown?" Gertrud asked with starry eyes. "We can afford such luxury?

Oswald nodded and lead her gently from the apartment, locking the front door before holding his arm out with a smile. Outside, a shiny black car await them at the curb, engine rumbling idly. In true gentlemanly fashion, he opened the door for his mother before climbing inside himself. The vehicle took them into the bustling heart of Gotham to a trendy restaurant Fish had recommended him. The lobby was packed with eager customers hoping to be placed on the waitlist, but Oswald simply strode up to the host and gave his name. They were lead to a small table lit with a candle, a bottle of champagne already chilling in a small bucket of ice.

Gertrude looked at the black car with wide eyes. “This is like magic, Oswald,” she cooed in awe. The leather lining of the car felt absolutely luxurious as she stroked it with an open palm.

She smiled at her darling boy and watched the lights of Gotham whiz by.

When they arrived at the restaurant Gertrudes eyes widened further. “My goodness!” They approached the table with Champagne at the ready. “Oswald this is too much~” she grinned.

“Not at all, I think you’ve deserved this for a long time, Ma,” the young man insisted. “Now I finally have the means to provide it.”

Gertrude looked at the menu, eyes nearly crossing at the complicated decorative language. Apéritif...Soupe à l’oignon...Boeuf bourguignon, she recognized only a few words at most in the whole menu. She knew she would make quite the fool of herself trying to pronounce these dishes. At last, she set the menu down and looked at Oswald. “Why don’t you pick, sweet boy? I am mixed up...so many choices.”  
Oswald took the menu from her gently, surveying the various options for a moment before closing it, having made his decision. “Would you like a drink with your meal, Mother?” he asked, flagging down a nearby waiter.

She nodded. “You know I like white wines, or gin,” she murmured softly, eyes downcast.

The waiter arrived, looking suitably pompous in his tails and bowtie. He opened the champagne for them and allowed Oswald to sample before pouring for them both. “Would the monsieur like to start with a soup or salad?” he asked as if nothing in the world would give him greater pleasure than fetching Oswald’s heart’s desire.

“We will both start with the french onion soup” he requested, allowing the man to take up the menu. Gone were his days of timid ‘pleases’ and ‘thank yous’- he was finally getting some respect and it felt wonderful, almost intoxicating. A live band played the strings beautifully in the background amidst the dull chatter of the dimly lit restaurant, the faint smell of expensive cigars wafting from the exclusive upscale booths near the back. High society was something that had always felt unattainable, yet here he was, being regarded with all the esteem being Fish Mooney’s umbrella boy granted him.

Dazzled by her son’s elegant ease with the waitstaff Gertrude smiled widely at her boy. “Onion soup, we might’ve had that at home,” she joked, intrigued by the concept of ordering ‘cuisine’.

“True, but would it be served to us in such style?” he replied, amused by his mother’s sense of humor. “Here they’ll wait on you hand and foot, you don’t have to lift a finger”. Oswald recalled days spent at his mother’s side in the kitchen, passing utensils and sampling bits and pieces along the way while she cooked for the two of them; her food was one of the few reliable comforts in his life.

She smiled softly at his description, truly charmed by the idea, for once, of her being waited upon. Privately, she often thought about days spent at the Van Dahl manor, serving Elijah and his awful family. Was this how one became so arrogant? She did not want Oswald to forget the people behind the service. “That sounds good, Oswald, we will make sure to take care of them, yes?”

“Yes, of course mother”, he assured. The man was not without manners after all, and it was no question that he be on his best behaviour around Gertrud. “I will see to it that they are compensated well for their service”. Though Oswald disliked the pompous air of the waitstaff, he would not withhold what they were owed for quality service.

Quite pleased, Gertrude smiled widely at her son. “Jó,” she beamed. “Jó fiú vagy.”  
“Jó anyám van”, he replied, easily slipping into his native tongue as he cooed his reply. She had truly put her entire self into raising him, he had only her to thank for his good fortune in life.

The rest of the meal was spent with pleasant conversation and amazing food. Gertrude was stuffed full by the time the bill came. Curious by nature she tried to sneak a peek at the total, only to be denied when Oswald snatched it up with a laugh. “It is not too bad, yes? I will feel terrible if you spent too much money on me, Oswald.”

Chuckling mischievously, he produced his wallet and tucked an undisclosed amount of cash into the folder before shutting it quickly. With his mother in mind, he left a generous tip. “I suppose you’ll never know~” he teased her.

“I am so happy you’re doing so well, Oswald, but I cannot help but fret~It’s a mother’s way.” She stood and had her coat put on for her by the attendant. “Oh! How lovely, thank you,” she replied softly.

Offering her his arm, they made the short walk to the curb where their vehicle was pulling up, helping her into the cab and sliding in beside her. Feeling tired from the food and wine, he rest his head gently upon her shoulder, rubbing his cheek tenderly against the woolen fabric of her coat. “Thank you for joining me, Mother. Tonight was lovely,” Oswald sighed contentedly, fingers playing absently with the soft golden curls that hung from her head. It felt good to relax and enjoy the fruits of his labour, if only for a night.

“The pleasure was mine, Oswald,” she replied in kind. “You truly are a wonderful son. I am so proud of you.” She leaned down, kissing the crown of his perfect little head.

-

That night, Oswald lay in bed, eyes following the pale yellow headlights that slowly slid across the cracked ceiling, cars moving steadily past; the night life bustled, an occasional sharp honk piercing the dull rumble of the city. It had been a magical evening, a taste of a life he now craved desperately. How easily he commanded respect as a simple umbrella boy, Oswald could only dream of the life he could have were he something more- could his name someday carry the same weight as Fish?

‘Oswald Chesterfield Cobblepot’

The middle name was his grandfather’s, a suggestion from Gertrud the young man had been all-too happy to accept, feeling as though he’d been deemed worthy enough to carry the name. Turning onto his side, he smiled as his eyes fell upon a framed photograph. It was old and weathered, bearing the smiling faces of a young couple; Getrud was unmistakable even in her youth, and the man beside her with an arm tight about her waist bore a striking resemblance to Oswald, one that brought him an indescribable amount of peace. Settling in, he succumbed to sleep at last, drifting away with a content smile on his lips. He dreamed of conquest, of flashy suits and shiny cars, men and women alike fawning for his approval as he ruled over Gotham with an iron fist.

A boy could dream.

 

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	6. Chapter 6

**Summary for the Chapter:**

> Things are coming to a head for Oswald as he meddles in things he ought to keep his beak out of.

“No, I won’t risk it. My men are spread thin as it is- I don’t need guns to negotiate with Carmine Falcone.” 

Long nails clinked rhythmically against the long stem of a half-empty wine glass, golden rings glinting with each shift of the lights on stage. Fish had no plans to violently overthrow her mentor, not if she had her way; Carmine deserved the opportunity to step down on his terms, pass along the torch as it were. 

Perched behind her chair, Oswald stood at attention with the carafe of wine, leaning over her shoulder to refill her glass. He grit his teeth silently as he listened to her casual refusal- an entire cargo shipment of weapons from the mainland? Even if she wasn’t interested in the weapons, declining a share meant more guns in the hands of their enemies! Fish was being blinded by her sentiment for the old man, Oswald thought, sinking behind her once more. 

“The shipment arrives at the docks tonight. If you change your mind send word within 48 hours; otherwise, I will assume you’ve decided to decline my offer.” The seedy-looking man stopped by the bar to knock back a shot, chatting with the bartender for a few minutes before disappearing out the front door. 

“Oswald, honey, would you be a sweet dear and fetch mama a snack from the kitchen? You know what I like~” Her voice was a soft coo, fingers creeping up his lapels to pat his cheek. 

“Yes, of course,” he replied, voice betraying his concealed ire. “Sweet or savory?” It wasn’t an unusual request. Though a coveted position, the role of ‘favorite’ came with certain expectations from Fish, subservience was one of them.

“Sweet please~”

The smile slid from his lips the moment he ducked out of sight, slipping into the kitchen with narrowed eyes. “Miss Mooney would like some chocolate-dipped strawberries. Quickly now- let’s not keep her waiting,” he demanded, helping himself to a beer from the oversized fridge humming in the corner. Oswald savored the power he held over the subordinate staff of the nightclub, a small taste of what was to come. Despite his recent emergence as Fish Mooney’s ‘pet,’ he was making a name for himself. 

“Here you are,” he smiled, having returned from the kitchen to place a plate of fresh, chilled strawberries before his mistress, along with a small bowl of melted chocolate.

“Thank you, baby,” she replied, helping herself immediately. 

The tiresome buffoon Fish had been arguing with appeared to have gone, but the entire exchange had left a bad taste in Oswald’s mouth. He knew she was making a terrible mistake in not taking every precaution available. Her soft spot, whatever it may be, for Carmine would be her undoing, as Falcone certainly had no qualms about using every ounce of his abilities against his enemies. 

Where did that leave Oswald then, once the bullets began to fly? He was one of Fish’s most trusted allies, and everyone knew it. Her ‘pet,’ as they called him, the little penguin. He resented it even as he knelt by her side. Lost in his reverie his face must’ve shown some sign of distress, a soft scowl, a furrowed brow because Fish leaned down and touched his pale, damp cheek. 

“Oswald, child, are you all right? You look ill.” 

He startled at her touch, looking up with wide blue eyes. “N-No, I’m fine, Ms. Mooney, it’s jus-” He stopped himself, biting his tongue sharply to keep from blurting out his thoughts; the ever-lurking fear, and tumbling uncertainty in his contriving brain. 

Fish narrowed her eyes, chin rising as she gazed down at her umbrella boy. “If you have something to say, Oswald, speak.” Her tone was low; voice set deep in her throat, which put Oswald on edge. As she sat back in her chair, a single brow raised, he sat up on his knees, licking his lips nervously before speaking. Her undivided attention was not difficult to attain, but the subject matter was much more severe than their usual banter.

“I believe you’re making a mistake.” 

She took a slow sip of wine, the silence around them filling Oswald’s veins with ice. As she set the glass down with a clink, she observed him with a reproving smirk. “You think I should’ve taken the guns.” 

He nodded emphatically, swallowing around the lump in his throat as her dark eyes picked him apart. 

With a long sigh of disappointment, she gazed up at the lights on the stage and took another drink. “Oswald, dear, you have much to learn about dealing with men. A man will argue and fight with you until he is blue in the face. He will speak over you, belittle you, and play the victim, but as soon as you raise your voice to a man you’ve lost. Carmine Falcone is many things, but he is still a man. If I attack him with force, he will retaliate with a power much greater than my own.” She leaned forward, taking Oswald’s chin in hand, gold lips sparkling in the low light, the smell of wine wafting strongly through his nose. “With men, you have to make it seem like they are the ones making the decision. Give him no other option, and the city shall be mine.” She shoved him away roughly, causing the boy to lose his footing, leaving him sprawled out on the floor at her feet. 

“You can go.” 

He pulled himself to his feet, face burning as he sputtered a hurried apology, avoiding his mentor’s russet gaze. Her words burned through him like a fire, blazing out of control through his thoughts as he took the long way home. 

Oswald, dear, you have much to learn about dealing with men.

After everything she had done to help him in his journey to become Oswald, to now act as though he was not the same as the men she had spent her life outwitting and manipulating? She was giving him advice as though he were another woman, sharing the juicy secrets to being a femme fatale; he felt foolish to have put so much trust in her opinion of him. His anger grew as he realized his position at her side was not one to be proud of, as he had once thought- she had turned him into a pet, an oddity to be displayed and exploited! He kicked a discarded bottle hard, glass shattering terrifically against the cracked concrete wall of the alleyway. The shards crunched underfoot as he stomped in the direction of his home. How had he not seen it before? Fish was never so tender towards Butch, nor any of her other male lackeys. 

A gunshot sounded somewhere in the distance, pulling the young man from his tantrum for a brief moment, an audacious plan suddenly unfolding in his brain. If Fish refused to see him as a man, then he would force her to take him seriously, one way or another,

Turning on his heel, he changed course, making his way back to the nightclub. Fish had evidently retired for the evening if the throaty moans echoing down the dark hallway were any indicator. Scowling, he moved silently through the dimly lit building, pushing his way out into the back alley where he knew several henchmen would be sharing a bottle of booze and passing around cigarettes. 

“Good evening,” he greeted, putting on an air of confidence as he moved into the light of the burning trashcan the toadies were huddled around. “Would any of you lovely gentleman be interested in joining me at the docks this evening to receive a shipment? Short notice, but Miss Mooney has her reasons for everything; I’m sure you’re aware.”

It was an effortless lie, the semi-intoxicated grunts had no qualms following the small man out to the pier under nightfall, pulling a sizeable rented truck up to the warehouse. Wisely, Oswald remained in the cab, gleefully pulling strings as his puppets, his men, took care of the heavy lifting, loading the ammunition and weaponry into the back. 

With the first half of his plan complete, he smiled at the small group of men, presenting them with a bottle of high-end vodka before he dropped them off at the nightclub, smirking to himself as he imagined the scene that Fish would undoubtedly uncover in the morning. Gripping the wheel tightly, he navigated the dark alleyways, carefully avoiding what appeared to be a massive crime scene unfolding, if the amount blue and red lights were any indicator. Stowing the truck away in a storage unit, carefully reserved with a pseudonym, Oswald went home for the night, eager to witness the chaos that would inevitably occur at Fish Mooney’s establishment the next morning. 

Oswald arrived the next afternoon with large coffee for himself and Butch, sliding the hot styrofoam cup towards him with a nod as he passed the bar. Everyone was whispering to each other covertly, heads tilted, their eyes shifting as they discussed what the surprise that had been found in the alleyway behind the building that morning. Masking his excitement, he climbed the stairs to the stage, slipping behind the piano to begin a piece he knew by heart, one of the first he had learned when his mother signed him up for lessons so many years ago. The melody unfolded at his fingertips, and he lost himself a moment in the tune, a faint smile clinging to his lips as he pondered the significant changes he had made since his journey began; there was still more to be discovered, he was sure. This was the beginning of something new.

Fish Mooney entered thirty minutes later with a flourish, snapping her fingers to gain her henchmen’s attention. All eyes on her she had Butch drag in Raul by the collar, throwing him down at the foot of the stage. “This is what happens to men who betray me,” she murmured icily. “Raul and I are going to have a little chat outside. Oswald,” she snapped, brown eyes sharp and severe. “Do be a dear and fetch mama’s umbrella.” 

Fingers slipping from the keys discordantly, the young man whipped his head toward the door, horrified to find that one of his pawns had survived. He improvised a finish for his piece and slipped off the stage, ice filling his veins as Raul lifted his head with a groan. “Of course Miss Mooney,” he nodded, quickly skirting out of the room. How had he survived?

By the time Oswald returned to the front of house Fish had Raul taken out back, her boys warming him up for their chat. Raul could be heard crying out, the dull thud of fists hitting flesh, and the sharp laughs of Fish’s boys accompanied his pleas for mercy. Fish smiled thinly as Oswald appeared, bright eyes narrowed as she lifted her bat. “Let’s go, dear, I haven’t got all day.” 

Swallowing his nervousness, he skittered after her with the requested umbrella tight in his fists. He unfurled it over her as he slipped past to open the door, and lamented internally as the rain dampened his carefully styled hair. His previous panic had mostly subsided, convinced that the chances of Fish believing anything Raul had to say to her were slim. A smug, evil grin spread over his cheeks as he watched Butch give the insignificant pawn another kick in the ribs. Never before had he felt so powerful. 

Fish thanked Butch for keeping him warm, a vicious smile on her painted lips. Taking up the bat, she jabbed Raul in the ribs. “What happened to my men, Raul?”

“I...I don’ know,” he slurred, crying in pain. 

She jabbed him again, watching with grim satisfaction as he fell to his hands and knees.

“I still care for you very deeply, Rail, but I don’t believe you care for me anymore.” Another jab and another pained groan left his broken lips. 

“Then tell me what happened.” 

His eyes flickered up to Oswald briefly before trailing down to the floor. “I...I don’ know. I came back from the bathroom an’ they were dead!” He cried out again as she struck him, the man falling to his side in the grimy puddles collecting in the alley. 

Excellent. He was as clueless as Oswald hoped he would be, stupid drunk. If he survived Fish’s inquisition, he would take care of the idiot himself afterward, clean up his mess. It was thrilling, in a way, playing such a dangerous game. If he was discovered too quickly, his chances of building an empire were slim- he would have to tread even more carefully now. 

Fish scowled as raindrops fell on her very expensive hair. “Boy!” she snapped, gaining Oswald’s attention from where it had strayed. He was distracted, looking at Raul with apparent interest; he forgot the umbrella, now above his head. 

“Sorry Miss Mooney…” he murmured, shifting the apparatus above her once more as the rain continued to drizzle down above them. He could ignore the weather, for now, there were more important details to attend to. He bared his yellow teeth in a menacing smile, one that suggested to Raul it might be in his best interest to keep silent. 

She pointed a well-manicured finger in his direction, the threat easily understood. “If you let this hair go frizzy you will be.”

One of the bartenders came out, rain immediately soaking his maroon uniform. He leaned in and murmured, “Detectives Bullock and Gordon are here to see you, Miss Mooney.”

Fish smiled and handed the bat over to Butch. “I’ll be right back. Keep him warm for me~” She turned, sauntering off with the barman back into the club. 

Raul lay pitifully on the ground, hands trembling from pain or the cold Gotham weather. Butch smiled as he regarded Oswald and held the bat out to him. Perhaps it was time the boy moved up in the world. “Hey Oswald, do you want a swing?” 

Oswald took the offered weapon with a devious chuckle, balancing his umbrella in one hand as he took a few sharp swings- none hard enough to kill the man, Oswald lamented his lack of strength- it would solve everything if he ‘accidentally’ killed him. 

Butch allowed him a few swings but grew progressively concerned over Oswald’s aggression. Fish still needed answers or at the very least a personal retribution. “Woah, Oswald buddy, take it easy.”

“Yeah,” another of Fish’s thugs chimed in. “Take it easy, Penguin.” 

His smile fell immediately, sneering in their direction with a prickly expression. “You know I don’t like to be called that.” Being one of the boys meant being insulted like one, but he already rather detest the prominence of his nose, he didn’t need to be compared to any sort of bird, much less a wobbly, un-intimidating arctic bird like a penguin. 

“Ooh, scary~” the other man sneered, not at all intimidated by the tiny man. 

Oswald raised the bat, a snarl forming about his lips when another voice cut through the alley. “How’s everyone doing out here?” The man cut a fine figure, dressed in a fitted suit and tie. He surveyed the people before him with a critical eye but made no move against them. 

“Who are you?” Butch asked with a charming grin.

“James Gordon, G.C.P.D,” he answered, eyes trailing from Oswald to Butch. 

“Oh, you came with Harvey then,” Butch replied smoothly as if they had been having a picnic instead of beating a man. “Glad to know you, James. I’m Butch Gilzean.”

James Gordon sneered and turned his attention back to Oswald once more. “Drop the bat.”

Oswald looked the man over once, then allowed the aluminum weapon to fall from his hands with a curious expression. What on earth did a rookie cop think he was doing giving orders to Fish Mooney’s men? How interesting.

“Oh, come now James, Raul, and Oswald here were just having a little fun.” He slapped a large hand on Raul’s shoulder, causing the bloodied man to startle and looked up. “Weren’t you boys~?”

“Y-yes...fun…” Raul stuttered, blood dripping from his nose and mouth as he gave a shaky thumbs-up. 

Jim looked away, brows furrowed as he glanced at Oswald. 

He smiled, amused by the serious expression on the young officer’s face. James Gordon~ A name as strong as his jawline, Oswald suddenly found himself rather self-conscious of his appearance, teeth disappearing behind a tight-lipped smile as he continued to keep eye contact with the rookie. Finally, he thought to himself; perhaps he had found himself a perfect adversary. This new officer was already in defiance the usual ways and seemed set out to defy the pecking order just as Oswald was determined to overthrow the underworld.

“You’re new here, eh? How do you like Gotham so far?” 

James smiled thinly when trailing back over to Oswald before settling on Butch once more. “Well enough.” He shook his head slightly, turning back toward the club. “See you around…”

Once James disappeared, Butch dropped Raul back into the puddle, a smirk about his lips. “Now, where were we~?”

Fish returned five minutes later with a self-satisfied grin. 

“Good visit with Harvey?” Butch asked, handing the bat back over to her. 

“Productive, yes.” She looked down at the heavily wounded Raul, eyes narrowing slightly before trailing back up to Butch. She pursed her lips, clearly unimpressed with the display. “I expect a satisfactory answer from you, Raul, or my brute Butch and his bat will be the least of your concerns. Oswald, come with me.”

He resisted the urge to celebrate his victory with a smile, following after his benefactor silently for a moment before inquiring about his curiosity. “James Gordon… new to Gotham, isn’t he?” Oswald asked, a wry grin betraying his eager curiosity. He wanted to know everything about him. 

“Yes, and he seems troublesome. Though, so did Harvey when he first started~” she grinned, looking back at her boy with a wink. 

He winked back, swallowing his pride as he continued to play the role of pet to Fish Mooney. “He didn’t give you any trouble, did he?” Oswald asked innocently as he cupped her hand, fingers gently running over each studded ring that adorned her fingers.

“Never, darling. Harvey will keep him in line, I’m sure.” She stopped in her office, directing Oswald to shut the door. “I have to make a phone call, sweets. Would you be a dear and rub my feet?”

Sucking in a quiet breath, he summoned up his most pleasant smile as he knelt before her, jaw tight as he slipped off her glittering heels and began his task. His mind was elsewhere, six steps ahead as he continued his plot to overthrow the woman that helped create him- no, he reminded himself, he created Oswald Cobblepot, she had provided the means. He had put in the time, the tears, countless nights spent worrying over his future; he deserved the credit. 

Settling back in her throne, Fish lifted the phone and spun the gilded dial. “It’s me,” she murmured. “Bullock is willing. I’ll have my men on it right away, sir. Absolutely, I shall inform you when it’s done. Goodnight.” 

With a satisfied grin, she sat back, hanging up the phone. “Everything is falling into place, Oswald.” Gently she extracted her foot from his careful work and stood, moving to her safe. With her back to Oswald, she put in the code and opened the door with a loud thunk. Slowly she removed a length of pearls, a facsimile to be sure, but a convincing enough copy. 

“Do you know what these are, Oswald~” 

He eyed the shimmering strands curiously. “Anything to do with our dear friends from the GCPD’s visit?” Oswald replied promptly, sinking into the smaller chair opposite her. He had heard few details of the high-profile murder investigation that was underway, but suspected Fish had already found a way to spin the tragedy in her favor. 

“A bit, yes,” she smirked. “This is the first trapping for Carmine: Martha Wayne’s pearls. Soon, pet, soon I’ll be in charge, and things are gonna change around here.”

The smile that spread across his cheeks was genuine; Fish was setting herself up for her demise. It would be easy enough to sow seeds of dissent, whisper the truth to a few well-placed ears, and she would be out of the picture, leaving himself to ease Carmine into retirement. He could scarcely believe his luck, sitting back on his knees with a content sigh as he looked up at Fish. It wouldn’t be much longer before he was demanding foot rubs and other finery from atop his throne.

“A new era is upon us,” he chirruped passively, encouraging his patron with thinly veiled lies. 

She grinned, looking down at Oswald with barely concealed excitement. She passed by him a hand grazing his cheek as she returned to her desk. “Fetch Butch for me, would you, love? I need to set some things in motion.” 

With a tight grin that was beginning to make his jaw ache, Oswald rose to his feet and left Fish’s office in search of Butch. The big man was sitting hunched over at the bar; a large black book spread before him. As Oswald approached, Butch shut the ledger and turned to the other man with a softly exasperated expression. 

“Hey, Oswald. You doing all right, man? Back there with Raul-” 

Oswald held up his hand impatiently. “As I told that rookie detective, Butch, it was all in fun. I got a little carried away.” He sat down, arm slung over the bartop as he attempted a look of casual nonchalance. “Did he end up saying anything?” 

“No,” he huffed softly. “Unlikely too now either, and Fish ain’t gonna be too happy about that.” 

Oswald concealed a grin of triumph. So, the idiot had finally expired, and perhaps Butch would take the fall for being too enthusiastic with the interrogation. He placed a conciliatory hand on his forearm, patting twice before removing the touch altogether. “I’m sorry, for whatever trouble my mistake may cause you...I could talk to Fish...?” 

“Nah, kid. It’ll be all right. Just keep your head low for a little while, okay? Somethings are gonna be shifting soon, and I don’t want you caught in the crossfire. You’re a good kid.” 

It was sweet, infantile language like that which both endeared Butch to Oswald and infuriated him. He would show them all how far he could rise! 

“Fish wanted to see you,” he murmured by way of a reply, removing himself from the barstool. “Best not to keep her waiting.” 

Butch shook his head with a sigh. That kid was such an oddball. 

Walking briskly down the street, Oswald navigated the afternoon crowds clustered on the sidewalk as he made his way toward an indiscriminate car parked by the curb ahead. Without hesitation, he slipped into the back seat, not bothering to remove his glasses. A grin spread upon his face as he informed the occupants of Fish’s wrongdoings, pulling another string in his tapestry of war. 

Fish giggled in delight as the comedian on the stage performed his act skiddishly. He seemed almost afraid of the mic, absolutely no stage presence. Oswald sat unimpressed in a booth off to the side after serving his benefactor her dinner.

Just as the hack was nearing what Oswald assumed was his closing bit, Fish’s phone rang. The woman’s clawed finger rose, silencing the act. 

“Yeah? Put him on.”

Oswald stood to refill her glass, eavesdropping. She dismissed him with an impatient wave of her hand. She responded to whoever was on the other end of the phone, an air of detached contempt dripping from her relaxed posture. 

“For a long time, until today. I did a big favor for you and your pals.”

The cops then, Oswald surmised. He sat forward in his seat. 

“And now it’s gonna blow up in my face on account of your stupidity.”

Something made her sit up straighter, shoulders back and tense. “How did they get on to me?”

Oswald’s eyes narrowed, pink tongue licking dry lips. 

“Huh. Not one of my people.” She turned trailing a critical eye over Oswald. He smiled softly, blue eyes wide and innocent. Not me. Don’t look here.

“True.” The tension drained from her body as she turned back toward the stage. Oswald suppressed a sigh of relief, watching as she rested back comfortably against her throne. “Put Butch back on, honey.” She leaned forward, a snarl curling her lips. “That son of a bitch just threatened me. String him up along with his partner!”

Harvey then. Good, he was a scruffy moron, and with him gone Oswald was getting rid of another loose end. He stood once more and topped off her wine. She smiled sweetly at him and cooed, “Bless your heart. Would you be a sweet boy and rub my feet.”

With a stilted smile, he bowed on his knees and removed her shoe gently. She dismissed the comedian with some cheap platitudes, giving her full attention to Oswald. 

“This amateur nonsense is a good sign. There used to be some discipline in this town.” She sighed softly, looking wistful. “It’s time. Somebody has to take over; it might as well be me.” 

He nodded sympathetically. “Yes, it might as well.”

“You know,” she murmured, warm brown eyes trained on Oswald’s light ones. “You’re like a son to me, Oswald.”

He felt many things for the woman who sat like a queen before him, but a familial bond was not one of them. He was indebted to Fish, grateful to her. Even after speaking to the MCU and setting his plans in motion to leave her in the dust, he could not deny all she had done for him. However, as she had once told Oswald, nothing in life is free, and he had paid for her help and guidance with his subservience and ridicule. 

Fish did not understand the meaning of the word ‘motherly’. Oswald’s mother was kind, supportive, and lofted Oswald up rather than belittle his efforts to climb. Fish treated him like a pet, a thing to be used, coddled, and discarded depending on the crime lord's mood. He needed to keep playing the game, string along his mentor long enough to lull her into making a mistake, and then he would take command. 

“I feel the same way.” 

“Which is why I don’t understand. After all I’ve done for you,” she began, an edge to her tone as sharp as a knife. “And right when I’m on the verge of great things, you betray me.”

He attempted a look of confusion, heart pounding in his throat. 

“Why would you betray your mother?”

“I-I don’t know what you mean.”

“It was you,” she sneered. “You snitched to the MCU. You wanna know how I know? Because no one else saw me with the pearls. Only you.”

He rose, sweat breaking out over his brow. He trembled, but was attempting to keep his composure. How could it have all fallen so quickly!?

“It was Gilzean.”

She tsked, coming to rise with a dark smirk. “No. Gilzean is loyal.” 

“So am I! I would open a vein right now for you.”

She grabbed the steak knife from her supper and cleaned the blade, offering it to him with a smirk. “Open one then.”

He balked, mouth falling agape as she turned her back to him, unafraid of her pet.

“I uh- I was speaking poetically.”

“Prove your loyalty, my little penguin.”

“Please Ms Mooney,” he growled, voice trembling as he came to a terrible decision. “Please don’t!” He lunged for her with the knife as she ducked, lifting the chair to bring it against his side with a heavy blow. Once he was on the floor, she lifted the bat over her head, and gazed down at her little boy.

“You broke my heart!” Each word was punctuated by a blow of the bat to Oswald’s leg. She had taken him in, elevated him, allowed him to be himself, to be free, and he threw it back in her face! Her anger wasn’t quelled by his sobs as he rolled in agony before her. She needed to contact Carmine and sort this mess out.

**Notes for the Chapter:**

> I would like to give a special thanks to my dears Konner and Tori for helping me edit this chapter and providing much-needed insight!


End file.
